2-[2-(1H-Imidazol-3-ium-5-yl)eth­yl]-3-(pyridin-2-yl)-2H-imidazo[1,5-a]pyridin-4-ium bis­(perchlorate)

Türkyılmaz, M.; Baran, Y.; Özdemir, N.

doi:10.1107/S1600536811015625

organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1282

doi:10.1107/S1600536811015625

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2-[2-(1H-Imidazol-3-ium-5-yl)ethyl]-3-(pyridin-2-yl)-2H-imidazo[1,5-a]pyridin-4-ium bis(perchlorate)

Murat Türkyılmaz,^a Yakup Baran ^b and Namık Özdemir ^c ^*

^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

(Received 23 April 2011; accepted 25 April 2011; online 29 April 2011)

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

C₁₇H₁₇N₅²⁺·2ClO₄⁻
M_r = 490.26
Monoclinic, P 2₁ /c
a = 15.044 (6) Å
b = 11.303 (4) Å
c = 12.783 (5) Å
β = 108.009 (15)°
V = 2067.1 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.37 mm⁻¹
T = 273 K
0.35 × 0.20 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
19199 measured reflections
4507 independent reflections
2540 reflections with I > 2σ(I)
R_int = 0.083

Refinement

R[F² > 2σ(F²)] = 0.074
wR(F²) = 0.214
S = 1.07
4507 reflections
363 parameters
198 restraints
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.52 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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⋯O6A^iv	0.93	2.43	3.139 (8)	133
Symmetry codes: (i) -x, -y, -z+1; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x, y+1, z; (iv) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: PROCESS-AUTO (Rigaku, 1998 ); cell refinement: 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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811015625/hb5862sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811015625/hb5862Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811015625/hb5862Isup3.cml

checkCIF report

Comment top

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).

Related literature top

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 top

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.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: 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).

Figures top

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.

2-[2-(1H-Imidazol-3-ium-5-yl)ethyl]-3-(pyridin-2-yl)-2H- imidazo[1,5-a]pyridin-4-ium bis(perchlorate) top

Crystal data top

C₁₇H₁₇N₅²⁺·2ClO₄⁻	F(000) = 1008
M_r = 490.26	D_x = 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

Data collection top

Rigaku R-AXIS RAPID diffractometer	2540 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.083
Graphite monochromator	θ_max = 27.0°, θ_min = 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 top

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(F_o²) + (0.0979P)² + 0.8991P] where P = (F_o² + 2F_c²)/3
4507 reflections	(Δ/σ)_max < 0.001
363 parameters	Δρ_max = 0.45 e Å⁻³
198 restraints	Δρ_min = −0.52 e Å⁻³

Crystal data top

C₁₇H₁₇N₅²⁺·2ClO₄⁻	V = 2067.1 (13) Å³
M_r = 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)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	2540 reflections with I > 2σ(I)
19199 measured reflections	R_int = 0.083
4507 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.074	198 restraints
wR(F²) = 0.214	H-atom parameters constrained
S = 1.07	Δρ_max = 0.45 e Å⁻³
4507 reflections	Δρ_min = −0.52 e Å⁻³
363 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O6A^iv	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⁻
M_r	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
R_int	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
Δρ_max, Δρ_min (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).

Hydrogen-bond geometry (Å, º) top

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···O6A^iv	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

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Volume 67| Part 5| May 2011| Page o1282

doi:10.1107/S1600536811015625

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2-[2-(1H-Imidazol-3-ium-5-yl)eth­yl]-3-(pyridin-2-yl)-2H-imidazo[1,5-a]pyridin-4-ium bis­­(perchlorate)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

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)