organic compounds
2-[2-(1H-Imidazol-3-ium-5-yl)ethyl]-3-(pyridin-2-yl)-2H-imidazo[1,5-a]pyridin-4-ium bis(perchlorate)
aDepartment of Chemistry, Faculty of Science, Trakya University, 22030 Edirne, Turkey, bDepartment of Chemistry, Faculty of Arts and Sciences, Çanakkale Onsekiz Mart University, 17020 Çanakkale, Turkey, and cDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey
*Correspondence e-mail: namiko@omu.edu.tr
In the title molecular salt, C17H17N5+·2ClO4−, the dihedral angles between the fused-ring system and the pendant five- and six-membered heterocyclic rings are 6.4 (2) and 41.29 (19)°, respectively. The O atoms of both perchlorate anions are disordered over two sets of sites with occupancy ratios of 0.614 (8):0.386 (8) and 0.591 (7):0.409 (7). An intramolecular C—H⋯N contact occurs in the cation. In the crystal, the components are linked by N—H⋯O and C—H⋯O hydrogen bonds and π–π stacking interactions [centroid–centroid separation = 3.642 (3) Å].
Related literature
For background to the biological properties of imidazopyridine compounds, see: Kaminski & Doweyko (1997); Sanfillipo et al. (1988); Lhassani et al. (1999). For hydrogen-bond motifs, see: Bernstein et al. (1995).
Experimental
Crystal data
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Data collection
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Refinement
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Data collection: PROCESS-AUTO (Rigaku, 1998); cell PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).
Supporting information
10.1107/S1600536811015625/hb5862sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536811015625/hb5862Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536811015625/hb5862Isup3.cml
Histamine-HCl (8 mmol, 1.18 g) was dissolved in argon saturated methanol and the solution was placed on a magnetic stirrer at room temperature. 2-Pyridinecarboxaldehyde (10 mmol, 1.08 g) was dissolved in argon saturated methanol and this solution was added to the histamine solution slowly. The final solution was left on a magnetic stirrer and temperature was raised to 333 K and the solution was left there for 24 h. Solvent volume was reduced and the solution was left for crystallization. After several days, brown blocks of (I) were separated, which were collected and dried.
H atoms were positioned geometrically and treated using a riding model, fixing the bond lengths at 0.86, 0.93 and 0.97 Å for NH, CH and CH2 groups, respectively. The displacement parameters of the H atoms were constrained as Uiso(H)= 1.2Ueq. In the compound, the O atoms of the two perchlorate anions show positional disorder and the refined site-occupancy factors of the disordered parts, viz. (O1A—O4A/O1B—O4B) and (O5A—O8A/O5B—O8B), are 0.614 (8)/0.386 (8)% and 0.591 (7)/0.409 (7)%, respectively.
Data collection: PROCESS-AUTO (Rigaku, 1998); cell
PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).Fig. 1. The molecular structure of (I) showing 30% probability displacement ellipsoids. For the sake of clarity, only H atoms involved in hydrogen bonding have been included and only the major parts of disordered fragments are drawn. Hydrogen bonds are indicated by broken lines. |
C17H17N52+·2ClO4− | F(000) = 1008 |
Mr = 490.26 | Dx = 1.575 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 11579 reflections |
a = 15.044 (6) Å | θ = 3.1–29.6° |
b = 11.303 (4) Å | µ = 0.37 mm−1 |
c = 12.783 (5) Å | T = 273 K |
β = 108.009 (15)° | Block, brown |
V = 2067.1 (13) Å3 | 0.35 × 0.20 × 0.20 mm |
Z = 4 |
Rigaku R-AXIS RAPID diffractometer | 2540 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.083 |
Graphite monochromator | θmax = 27.0°, θmin = 3.1° |
Detector resolution: 10.00 pixels mm-1 | h = −19→19 |
ω scans | k = −14→14 |
19199 measured reflections | l = −16→16 |
4507 independent reflections |
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)] = 0.074 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.214 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0979P)2 + 0.8991P] where P = (Fo2 + 2Fc2)/3 |
4507 reflections | (Δ/σ)max < 0.001 |
363 parameters | Δρmax = 0.45 e Å−3 |
198 restraints | Δρmin = −0.52 e Å−3 |
C17H17N52+·2ClO4− | V = 2067.1 (13) Å3 |
Mr = 490.26 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 15.044 (6) Å | µ = 0.37 mm−1 |
b = 11.303 (4) Å | T = 273 K |
c = 12.783 (5) Å | 0.35 × 0.20 × 0.20 mm |
β = 108.009 (15)° |
Rigaku R-AXIS RAPID diffractometer | 2540 reflections with I > 2σ(I) |
19199 measured reflections | Rint = 0.083 |
4507 independent reflections |
R[F2 > 2σ(F2)] = 0.074 | 198 restraints |
wR(F2) = 0.214 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.45 e Å−3 |
4507 reflections | Δρmin = −0.52 e Å−3 |
363 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 | Occ. (<1) | |
Cl1 | 0.04647 (8) | −0.10009 (10) | 0.30270 (8) | 0.0598 (4) | |
Cl2 | 0.38314 (10) | 0.18832 (12) | 0.36810 (11) | 0.0791 (4) | |
O1A | 0.1400 (4) | −0.0618 (7) | 0.3141 (7) | 0.0894 (19) | 0.614 (8) |
O2A | −0.0092 (7) | −0.0565 (8) | 0.2027 (5) | 0.115 (2) | 0.614 (8) |
O3A | 0.0469 (7) | −0.2260 (4) | 0.3022 (9) | 0.091 (2) | 0.614 (8) |
O4A | 0.0210 (9) | −0.0453 (14) | 0.3907 (6) | 0.069 (2) | 0.614 (8) |
O1B | 0.0926 (10) | −0.0210 (9) | 0.2511 (10) | 0.096 (2) | 0.386 (8) |
O2B | −0.0448 (5) | −0.1148 (12) | 0.2321 (8) | 0.088 (3) | 0.386 (8) |
O3B | 0.0868 (11) | −0.2140 (7) | 0.3301 (15) | 0.092 (3) | 0.386 (8) |
O4B | 0.0434 (15) | −0.064 (2) | 0.4091 (8) | 0.064 (3) | 0.386 (8) |
O5A | 0.4484 (9) | 0.1176 (9) | 0.4445 (8) | 0.114 (3) | 0.591 (7) |
O6A | 0.3768 (6) | 0.2058 (7) | 0.2528 (5) | 0.113 (2) | 0.591 (7) |
O7A | 0.3632 (7) | 0.2974 (6) | 0.4153 (7) | 0.089 (2) | 0.591 (7) |
O8A | 0.2969 (5) | 0.1162 (7) | 0.3466 (6) | 0.0921 (19) | 0.591 (7) |
O5B | 0.4416 (12) | 0.0902 (12) | 0.4024 (12) | 0.105 (3) | 0.409 (7) |
O6B | 0.4497 (7) | 0.2597 (8) | 0.3319 (10) | 0.108 (3) | 0.409 (7) |
O7B | 0.3793 (11) | 0.2623 (10) | 0.4594 (8) | 0.089 (3) | 0.409 (7) |
O8B | 0.2861 (6) | 0.1717 (13) | 0.3009 (12) | 0.123 (3) | 0.409 (7) |
N1 | 0.2084 (2) | 0.6878 (3) | 0.5373 (3) | 0.0568 (9) | |
N2 | 0.2744 (2) | 0.8592 (3) | 0.5682 (3) | 0.0525 (8) | |
N3 | 0.3643 (3) | 0.6138 (3) | 0.4591 (3) | 0.0678 (10) | |
N4 | 0.1981 (3) | 0.2840 (3) | 0.4732 (3) | 0.0602 (9) | |
H4N | 0.2431 | 0.2966 | 0.4465 | 0.072* | |
N5 | 0.0837 (3) | 0.2016 (3) | 0.5074 (3) | 0.0703 (11) | |
H5N | 0.0406 | 0.1515 | 0.5070 | 0.084* | |
C1 | 0.1678 (3) | 0.7453 (4) | 0.6032 (3) | 0.0633 (12) | |
H1 | 0.1215 | 0.7153 | 0.6299 | 0.076* | |
C2 | 0.2065 (3) | 0.8542 (4) | 0.6235 (3) | 0.0586 (11) | |
C3 | 0.1957 (4) | 0.9540 (5) | 0.6846 (4) | 0.0705 (13) | |
H3 | 0.1515 | 0.9533 | 0.7218 | 0.085* | |
C4 | 0.2487 (4) | 1.0493 (5) | 0.6890 (4) | 0.0786 (15) | |
H4 | 0.2398 | 1.1161 | 0.7270 | 0.094* | |
C5 | 0.3187 (4) | 1.0491 (4) | 0.6361 (4) | 0.0753 (14) | |
H5 | 0.3571 | 1.1151 | 0.6429 | 0.090* | |
C6 | 0.3313 (3) | 0.9565 (4) | 0.5763 (3) | 0.0616 (11) | |
H6 | 0.3771 | 0.9580 | 0.5414 | 0.074* | |
C7 | 0.2737 (3) | 0.7553 (3) | 0.5146 (3) | 0.0519 (10) | |
C8 | 0.3311 (3) | 0.7255 (4) | 0.4459 (3) | 0.0527 (10) | |
C9 | 0.3495 (3) | 0.8053 (4) | 0.3742 (4) | 0.0624 (11) | |
H9 | 0.3223 | 0.8800 | 0.3651 | 0.075* | |
C10 | 0.4094 (4) | 0.7724 (5) | 0.3157 (4) | 0.0763 (14) | |
H10 | 0.4256 | 0.8254 | 0.2691 | 0.092* | |
C11 | 0.4437 (4) | 0.6597 (6) | 0.3288 (5) | 0.0821 (16) | |
H11 | 0.4839 | 0.6347 | 0.2907 | 0.099* | |
C12 | 0.4184 (4) | 0.5831 (5) | 0.3986 (4) | 0.0814 (15) | |
H12 | 0.4404 | 0.5057 | 0.4037 | 0.098* | |
C13 | 0.1788 (3) | 0.5677 (4) | 0.4936 (4) | 0.0613 (11) | |
H13A | 0.2000 | 0.5529 | 0.4304 | 0.074* | |
H13B | 0.1112 | 0.5629 | 0.4697 | 0.074* | |
C14 | 0.2189 (3) | 0.4744 (4) | 0.5806 (4) | 0.0643 (12) | |
H14A | 0.2856 | 0.4673 | 0.5932 | 0.077* | |
H14B | 0.2091 | 0.4979 | 0.6492 | 0.077* | |
C15 | 0.1729 (3) | 0.3587 (4) | 0.5444 (3) | 0.0554 (10) | |
C16 | 0.1433 (3) | 0.1910 (4) | 0.4521 (4) | 0.0674 (12) | |
H16 | 0.1463 | 0.1285 | 0.4060 | 0.081* | |
C17 | 0.1007 (3) | 0.3047 (4) | 0.5659 (4) | 0.0660 (12) | |
H17 | 0.0683 | 0.3325 | 0.6122 | 0.079* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0669 (7) | 0.0630 (7) | 0.0559 (6) | 0.0019 (5) | 0.0283 (5) | −0.0003 (5) |
Cl2 | 0.0943 (9) | 0.0704 (8) | 0.0883 (9) | 0.0208 (7) | 0.0509 (8) | 0.0218 (6) |
O1A | 0.080 (3) | 0.106 (4) | 0.101 (4) | −0.012 (3) | 0.056 (3) | −0.012 (4) |
O2A | 0.137 (5) | 0.124 (5) | 0.068 (3) | 0.020 (4) | 0.006 (3) | 0.017 (3) |
O3A | 0.116 (6) | 0.064 (3) | 0.094 (5) | −0.010 (3) | 0.036 (5) | −0.007 (3) |
O4A | 0.072 (6) | 0.074 (5) | 0.072 (3) | −0.001 (4) | 0.040 (4) | −0.005 (4) |
O1B | 0.122 (5) | 0.102 (5) | 0.083 (5) | −0.009 (4) | 0.059 (4) | 0.011 (4) |
O2B | 0.090 (4) | 0.108 (6) | 0.057 (4) | 0.004 (4) | 0.010 (3) | −0.016 (4) |
O3B | 0.107 (7) | 0.069 (4) | 0.090 (6) | 0.020 (4) | 0.014 (6) | −0.004 (4) |
O4B | 0.071 (7) | 0.072 (6) | 0.050 (3) | −0.007 (5) | 0.023 (4) | −0.003 (4) |
O5A | 0.106 (4) | 0.092 (5) | 0.122 (6) | 0.031 (4) | 0.005 (5) | 0.007 (4) |
O6A | 0.149 (5) | 0.109 (5) | 0.102 (3) | 0.040 (4) | 0.071 (4) | 0.024 (3) |
O7A | 0.098 (5) | 0.061 (3) | 0.117 (5) | 0.006 (3) | 0.047 (5) | 0.009 (3) |
O8A | 0.098 (3) | 0.090 (4) | 0.084 (4) | 0.007 (3) | 0.022 (3) | −0.004 (3) |
O5B | 0.111 (5) | 0.082 (5) | 0.124 (7) | 0.034 (5) | 0.038 (6) | 0.013 (5) |
O6B | 0.139 (5) | 0.098 (5) | 0.118 (6) | 0.011 (4) | 0.087 (4) | 0.020 (5) |
O7B | 0.091 (5) | 0.083 (6) | 0.106 (5) | −0.001 (5) | 0.050 (5) | −0.003 (4) |
O8B | 0.117 (4) | 0.115 (7) | 0.114 (6) | 0.018 (4) | 0.002 (5) | −0.001 (5) |
N1 | 0.060 (2) | 0.056 (2) | 0.054 (2) | −0.0036 (17) | 0.0177 (18) | 0.0058 (16) |
N2 | 0.061 (2) | 0.052 (2) | 0.0438 (18) | 0.0022 (16) | 0.0154 (16) | 0.0031 (15) |
N3 | 0.073 (3) | 0.061 (2) | 0.066 (2) | 0.0037 (19) | 0.017 (2) | −0.0068 (19) |
N4 | 0.065 (2) | 0.058 (2) | 0.062 (2) | −0.0012 (18) | 0.0260 (19) | 0.0045 (18) |
N5 | 0.060 (2) | 0.057 (2) | 0.094 (3) | −0.0071 (18) | 0.024 (2) | 0.015 (2) |
C1 | 0.062 (3) | 0.077 (3) | 0.051 (2) | 0.002 (2) | 0.019 (2) | 0.011 (2) |
C2 | 0.058 (3) | 0.073 (3) | 0.043 (2) | 0.012 (2) | 0.013 (2) | 0.011 (2) |
C3 | 0.077 (3) | 0.086 (4) | 0.049 (2) | 0.019 (3) | 0.019 (2) | 0.000 (2) |
C4 | 0.099 (4) | 0.071 (3) | 0.060 (3) | 0.018 (3) | 0.017 (3) | −0.008 (2) |
C5 | 0.098 (4) | 0.054 (3) | 0.063 (3) | 0.000 (3) | 0.009 (3) | −0.005 (2) |
C6 | 0.078 (3) | 0.050 (2) | 0.054 (2) | −0.007 (2) | 0.017 (2) | 0.000 (2) |
C7 | 0.057 (2) | 0.049 (2) | 0.048 (2) | −0.0030 (19) | 0.0136 (19) | 0.0069 (18) |
C8 | 0.054 (2) | 0.053 (2) | 0.049 (2) | −0.0041 (19) | 0.0132 (19) | −0.0070 (19) |
C9 | 0.065 (3) | 0.071 (3) | 0.053 (2) | −0.007 (2) | 0.022 (2) | −0.008 (2) |
C10 | 0.077 (3) | 0.092 (4) | 0.063 (3) | −0.027 (3) | 0.025 (3) | −0.010 (3) |
C11 | 0.063 (3) | 0.105 (5) | 0.085 (4) | −0.014 (3) | 0.033 (3) | −0.031 (3) |
C12 | 0.071 (3) | 0.084 (4) | 0.086 (4) | 0.007 (3) | 0.020 (3) | −0.026 (3) |
C13 | 0.067 (3) | 0.055 (3) | 0.059 (3) | −0.014 (2) | 0.014 (2) | 0.007 (2) |
C14 | 0.074 (3) | 0.056 (3) | 0.061 (3) | −0.003 (2) | 0.017 (2) | 0.007 (2) |
C15 | 0.058 (3) | 0.056 (2) | 0.054 (2) | 0.000 (2) | 0.020 (2) | 0.006 (2) |
C16 | 0.072 (3) | 0.053 (3) | 0.073 (3) | −0.002 (2) | 0.017 (3) | 0.001 (2) |
C17 | 0.066 (3) | 0.065 (3) | 0.075 (3) | 0.004 (2) | 0.034 (3) | 0.008 (2) |
Cl1—O2A | 1.385 (5) | N5—H5N | 0.8600 |
Cl1—O2B | 1.401 (6) | C1—C2 | 1.352 (6) |
Cl1—O1B | 1.414 (6) | C1—H1 | 0.9300 |
Cl1—O3B | 1.420 (6) | C2—C3 | 1.410 (6) |
Cl1—O3A | 1.423 (5) | C3—C4 | 1.330 (7) |
Cl1—O4A | 1.436 (4) | C3—H3 | 0.9300 |
Cl1—O4B | 1.436 (5) | C4—C5 | 1.417 (7) |
Cl1—O1A | 1.435 (5) | C4—H4 | 0.9300 |
Cl2—O5B | 1.400 (6) | C5—C6 | 1.343 (6) |
Cl2—O5A | 1.401 (5) | C5—H5 | 0.9300 |
Cl2—O7A | 1.444 (5) | C6—H6 | 0.9300 |
Cl2—O7B | 1.452 (6) | C7—C8 | 1.448 (5) |
Cl2—O8B | 1.459 (7) | C8—C9 | 1.374 (6) |
Cl2—O6A | 1.461 (5) | C9—C10 | 1.388 (6) |
Cl2—O6B | 1.468 (6) | C9—H9 | 0.9300 |
Cl2—O8A | 1.484 (6) | C10—C11 | 1.365 (8) |
N1—C7 | 1.344 (5) | C10—H10 | 0.9300 |
N1—C1 | 1.350 (5) | C11—C12 | 1.379 (8) |
N1—C13 | 1.483 (5) | C11—H11 | 0.9300 |
N2—C7 | 1.358 (5) | C12—H12 | 0.9300 |
N2—C6 | 1.377 (5) | C13—C14 | 1.515 (6) |
N2—C2 | 1.411 (5) | C13—H13A | 0.9700 |
N3—C12 | 1.331 (6) | C13—H13B | 0.9700 |
N3—C8 | 1.349 (5) | C14—C15 | 1.486 (6) |
N4—C16 | 1.312 (6) | C14—H14A | 0.9700 |
N4—C15 | 1.377 (5) | C14—H14B | 0.9700 |
N4—H4N | 0.8600 | C15—C17 | 1.347 (6) |
N5—C16 | 1.307 (6) | C16—H16 | 0.9300 |
N5—C17 | 1.366 (6) | C17—H17 | 0.9300 |
O2B—Cl1—O1B | 107.4 (7) | C3—C4—H4 | 119.9 |
O2B—Cl1—O3B | 108.1 (7) | C5—C4—H4 | 119.9 |
O1B—Cl1—O3B | 117.0 (9) | C6—C5—C4 | 121.9 (5) |
O2A—Cl1—O3A | 110.7 (5) | C6—C5—H5 | 119.1 |
O2A—Cl1—O4A | 109.8 (6) | C4—C5—H5 | 119.1 |
O3A—Cl1—O4A | 116.0 (8) | C5—C6—N2 | 118.2 (4) |
O2B—Cl1—O4B | 109.4 (9) | C5—C6—H6 | 120.9 |
O1B—Cl1—O4B | 115.2 (12) | N2—C6—H6 | 120.9 |
O3B—Cl1—O4B | 99.4 (12) | N1—C7—N2 | 105.9 (4) |
O2A—Cl1—O1A | 106.3 (5) | N1—C7—C8 | 127.7 (4) |
O3A—Cl1—O1A | 107.2 (5) | N2—C7—C8 | 126.4 (4) |
O4A—Cl1—O1A | 106.3 (7) | N3—C8—C9 | 123.7 (4) |
O5A—Cl2—O7A | 112.8 (5) | N3—C8—C7 | 114.1 (4) |
O5B—Cl2—O7B | 112.5 (8) | C9—C8—C7 | 122.1 (4) |
O5B—Cl2—O8B | 120.0 (10) | C8—C9—C10 | 118.8 (5) |
O7B—Cl2—O8B | 105.4 (9) | C8—C9—H9 | 120.6 |
O5A—Cl2—O6A | 126.4 (6) | C10—C9—H9 | 120.6 |
O7A—Cl2—O6A | 110.4 (4) | C11—C10—C9 | 117.9 (5) |
O5B—Cl2—O6B | 96.3 (10) | C11—C10—H10 | 121.0 |
O7B—Cl2—O6B | 97.9 (7) | C9—C10—H10 | 121.0 |
O8B—Cl2—O6B | 122.8 (8) | C10—C11—C12 | 119.7 (5) |
O5A—Cl2—O8A | 101.5 (7) | C10—C11—H11 | 120.2 |
O7A—Cl2—O8A | 105.3 (5) | C12—C11—H11 | 120.2 |
O6A—Cl2—O8A | 96.1 (5) | N3—C12—C11 | 123.6 (5) |
C7—N1—C1 | 111.3 (4) | N3—C12—H12 | 118.2 |
C7—N1—C13 | 126.3 (4) | C11—C12—H12 | 118.2 |
C1—N1—C13 | 122.3 (4) | N1—C13—C14 | 110.9 (3) |
C7—N2—C6 | 129.5 (4) | N1—C13—H13A | 109.5 |
C7—N2—C2 | 108.9 (4) | C14—C13—H13A | 109.5 |
C6—N2—C2 | 121.5 (4) | N1—C13—H13B | 109.5 |
C12—N3—C8 | 116.1 (4) | C14—C13—H13B | 109.5 |
C16—N4—C15 | 110.1 (4) | H13A—C13—H13B | 108.1 |
C16—N4—H4N | 125.0 | C15—C14—C13 | 110.1 (4) |
C15—N4—H4N | 125.0 | C15—C14—H14A | 109.6 |
C16—N5—C17 | 109.3 (4) | C13—C14—H14A | 109.6 |
C16—N5—H5N | 125.3 | C15—C14—H14B | 109.6 |
C17—N5—H5N | 125.3 | C13—C14—H14B | 109.6 |
N1—C1—C2 | 107.9 (4) | H14A—C14—H14B | 108.2 |
N1—C1—H1 | 126.1 | C17—C15—N4 | 105.1 (4) |
C2—C1—H1 | 126.1 | C17—C15—C14 | 131.5 (4) |
C1—C2—C3 | 135.9 (5) | N4—C15—C14 | 123.3 (4) |
C1—C2—N2 | 106.0 (4) | N5—C16—N4 | 107.9 (4) |
C3—C2—N2 | 118.1 (4) | N5—C16—H16 | 126.0 |
C4—C3—C2 | 120.1 (5) | N4—C16—H16 | 126.0 |
C4—C3—H3 | 120.0 | C15—C17—N5 | 107.5 (4) |
C2—C3—H3 | 120.0 | C15—C17—H17 | 126.2 |
C3—C4—C5 | 120.2 (5) | N5—C17—H17 | 126.2 |
C7—N1—C1—C2 | 0.8 (5) | C12—N3—C8—C7 | −179.2 (4) |
C13—N1—C1—C2 | −176.6 (4) | N1—C7—C8—N3 | −41.5 (6) |
N1—C1—C2—C3 | −179.7 (5) | N2—C7—C8—N3 | 139.5 (4) |
N1—C1—C2—N2 | −1.2 (4) | N1—C7—C8—C9 | 138.6 (4) |
C7—N2—C2—C1 | 1.3 (4) | N2—C7—C8—C9 | −40.4 (6) |
C6—N2—C2—C1 | −176.5 (4) | N3—C8—C9—C10 | −3.5 (7) |
C7—N2—C2—C3 | −179.9 (4) | C7—C8—C9—C10 | 176.4 (4) |
C6—N2—C2—C3 | 2.4 (6) | C8—C9—C10—C11 | 3.0 (7) |
C1—C2—C3—C4 | 178.3 (5) | C9—C10—C11—C12 | −0.1 (7) |
N2—C2—C3—C4 | −0.1 (6) | C8—N3—C12—C11 | 2.4 (7) |
C2—C3—C4—C5 | −2.5 (7) | C10—C11—C12—N3 | −2.8 (8) |
C3—C4—C5—C6 | 3.0 (8) | C7—N1—C13—C14 | 104.7 (5) |
C4—C5—C6—N2 | −0.7 (7) | C1—N1—C13—C14 | −78.3 (5) |
C7—N2—C6—C5 | −179.2 (4) | N1—C13—C14—C15 | 167.9 (4) |
C2—N2—C6—C5 | −2.0 (6) | C16—N4—C15—C17 | 0.7 (5) |
C1—N1—C7—N2 | 0.1 (5) | C16—N4—C15—C14 | −177.3 (4) |
C13—N1—C7—N2 | 177.3 (3) | C13—C14—C15—C17 | −96.1 (6) |
C1—N1—C7—C8 | −179.1 (4) | C13—C14—C15—N4 | 81.3 (5) |
C13—N1—C7—C8 | −1.9 (7) | C17—N5—C16—N4 | 0.0 (5) |
C6—N2—C7—N1 | 176.7 (4) | C15—N4—C16—N5 | −0.4 (5) |
C2—N2—C7—N1 | −0.8 (4) | N4—C15—C17—N5 | −0.7 (5) |
C6—N2—C7—C8 | −4.1 (7) | C14—C15—C17—N5 | 177.1 (4) |
C2—N2—C7—C8 | 178.4 (4) | C16—N5—C17—C15 | 0.5 (5) |
C12—N3—C8—C9 | 0.8 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13A···N3 | 0.97 | 2.48 | 3.001 (6) | 113 |
C16—H16···O1A | 0.93 | 2.44 | 3.351 (8) | 167 |
N4—H4N···O7A | 0.86 | 1.97 | 2.807 (10) | 165 |
N5—H5N···O4Ai | 0.86 | 2.18 | 2.927 (16) | 145 |
C11—H11···O6Aii | 0.93 | 2.46 | 3.224 (9) | 139 |
C6—H6···O5Aiii | 0.93 | 2.60 | 3.331 (17) | 136 |
C5—H5···O6Aiv | 0.93 | 2.43 | 3.139 (8) | 133 |
Symmetry codes: (i) −x, −y, −z+1; (ii) −x+1, y+1/2, −z+1/2; (iii) x, y+1, z; (iv) x, −y+3/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C17H17N52+·2ClO4− |
Mr | 490.26 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 273 |
a, b, c (Å) | 15.044 (6), 11.303 (4), 12.783 (5) |
β (°) | 108.009 (15) |
V (Å3) | 2067.1 (13) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.37 |
Crystal size (mm) | 0.35 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 19199, 4507, 2540 |
Rint | 0.083 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.074, 0.214, 1.07 |
No. of reflections | 4507 |
No. of parameters | 363 |
No. of restraints | 198 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.45, −0.52 |
Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13A···N3 | 0.97 | 2.48 | 3.001 (6) | 113 |
C16—H16···O1A | 0.93 | 2.44 | 3.351 (8) | 167 |
N4—H4N···O7A | 0.86 | 1.97 | 2.807 (10) | 165 |
N5—H5N···O4Ai | 0.86 | 2.18 | 2.927 (16) | 145 |
C11—H11···O6Aii | 0.93 | 2.46 | 3.224 (9) | 139 |
C6—H6···O5Aiii | 0.93 | 2.60 | 3.331 (17) | 136 |
C5—H5···O6Aiv | 0.93 | 2.43 | 3.139 (8) | 133 |
Symmetry codes: (i) −x, −y, −z+1; (ii) −x+1, y+1/2, −z+1/2; (iii) x, y+1, z; (iv) x, −y+3/2, z+1/2. |
Acknowledgements
Financial support received from the Scientific and Technological Research Council of Turkey research program 1001 grant for 104 T389 is gratefully acknowledged
References
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Kaminski, J. J. & Doweyko, A. M. (1997). J. Med. Chem. 40, 427–436. CrossRef CAS PubMed Web of Science Google Scholar
Lhassani, M., Chavignon, O., Chezal, J.-M., Teulade, J.-C., Chapat, J.-P., Snoeck, R., Andrei, G., Balzarini, J., De Clercq, E. & Gueiffier, A. (1999). Eur. J. Med. Chem. 34, 271–274. CrossRef CAS Google Scholar
Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2004). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sanfillipo, P. J., Urbanski, M., Press, J. B., Dubinsky, B. & Moore, J. B. Jr (1988). J. Med. Chem. 31, 2221–2227. PubMed Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
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.
Imidazopyridine derivatives are of great importance because of their remarkable biological properties. For example, gastric antisecretory (Kaminski & Doweyko, 1997), local anesthetic (Sanfillipo et al., 1988) and antiviral (Lhassani et al., 1999) properties of imidazo[1,2-a]pyridine derivatives have been described.
The title salt comprises a double protonated 2-[2-(1H-imidazol-3-ium-5-yl)ethyl]-3-(pyridin-2-yl)-2H-imidazo [1,5-a]pyridin-4-ium cation and two perchlorate anion (Fig. 1). The interatomic distances and angles in the title salt show no anomalies.
The molecular structure of the title compound, (I), contains one intramolecular C—H···N contact leading to the formation of a six-membered ring with graph-set descriptor S(6) (Bernstein et al., 1995). In the crystal structure, intermolecular C—H···O and N—H···O type hydrogen bonds and π—π stacking interactions between the (N2/C2—C6) and (N3/C8—C12) pyridine rings interconnect the ions into a three-dimensional supramolecular structure (Table 1).