2-(2-Pyridyl)pyridinium perchlorate, redetermined at 120 K: complex hydrogen-bonded sheets

Kavitha, S.J.; Panchanatheswaran, K.; Low, J.N.; Glidewell, C.

doi:10.1107/S0108270105018810

organic compounds

STRUCTURAL
CHEMISTRY

ISSN: 2053-2296

Volume 61| Part 8| August 2005| Pages o473-o474

doi:10.1107/S0108270105018810

2-(2-Pyridyl)pyridinium perchlorate, redetermined at 120 K: complex hydrogen-bonded sheets

S. Jose Kavitha,^a Krishnaswamy Panchanatheswaran,^a John N. Low ^b and Christopher Glidewell ^c ^*

^aSchool of Chemistry, Bharathidasan University, Tiruchirappalli, Tamil Nadu 620 024, India, ^bDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland, and ^cSchool of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland
^*Correspondence e-mail: cg@st-andrews.ac.uk

(Received 9 June 2005; accepted 13 June 2005; online 9 July 2005)

In the title compound, C₁₀H₉N₂⁺·ClO₄⁻, the ions are linked into complex sheets by the combination of one N—H⋯O and four independent C—H⋯O hydrogen bonds.

Comment

The structure of the title compound, (I), was determined many years ago (Lipkowski et al., 1976 ); using diffraction data collected at ambient temperature, the structure was refined only to R = 0.072. We have now redetermined this structure using diffraction data collected at 120 K and report here a more precise determination, together with the interesting supramolecular structure of this compound. The space group and unit-cell dimensions confirm that the previous study and the present work involve the same phase.

The title compound (Fig. 1) is a salt, and in the selected asymmetric unit, the two ions are linked by an N—H⋯O hydrogen bond. In the cation, the dihedral angle between the two ring planes is 14.96 (15)°, similar to the value of 16.6° reported previously for the ambient-temperature structure (Lipkowski et al., 1976). In addition, there is a significant difference in the C—N—C angles at the protonated atom N11 and the unprotonated atom N21 (Table 1). In the anion, the Cl—O distance involving atom O1 is somewhat longer than the other Cl—O distances, possibly reflecting some modest localization of the negative charge.

In addition to the N—H⋯O hydrogen bond, involving the more negative atom O1 as the acceptor, there are a number of independent C—H⋯O hydrogen bonds (Table 2). Although these all have fairly long H⋯O distances, they all appear to have some structural significance, including the effective tethering of the perchlorate anion, for which the anisotropic displacement parameters give no indication of significant libration, far less of the type of disorder for which this anion is notorious. Hence, we conclude that these interactions are significant. All of the hydrogen bonds involve donors in the protonated pyridinium ring, leading to more acidic X—H bonds (X = C or N), and all four O atoms of the anion act as acceptors, so precluding any significant librational motion for the anion.

The C—H⋯O hydrogen bond involving atom C16 as the donor reinforces the N—H⋯O hydrogen bond in linking together the two independent ions, so forming an R₂²(7) motif, and the combination of this and the interaction having atom C13 as the donor then generates by translation a C₂²(8)C₂²(9)[R₂²(7)] chain of rings running parallel to the [10 $[\overline{1}]$ ] direction (Fig. 2). The two hydrogen bonds having atoms C14 and C15 as the donors act co-operatively to form a zigzag chain of edge-fused rings running parallel to the [20 $[\overline{1}]$ ] direction and generated by the c-glide plane at y = 0 (Fig. 3). The combination of the [10 $[\overline{1}]$ ] and [20 $[\overline{1}]$ ] chains then generates a complex (010) sheet.

Figure 1
The independent components of compound (I)

, showing the atom-labelling scheme and the N—H⋯O hydrogen bond (dashed line). Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.

Figure 2
Part of the crystal structure of (I)

, showing the formation of a hydrogen-bonded chain of rings along [10 $[\overline{1}]$ ]. For the sake of clarity, the H atoms not involved in the motif shown have been omitted. Atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (x − 1, y, 1 + z) and (1 + x, y, z − 1), respectively.

Figure 3
Part of the crystal structure of (I)

, showing the formation of a hydrogen-bonded chain of rings along [20 $[\overline{1}]$ ]. For the sake of clarity, the H atoms not involved in the motif shown have been omitted. Atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (x − 1, −y, $[{1\over 2}]$ + z) and (1 + x, −y, z − $[{1\over 2}]$ ), respectively.

Experimental

2,2′-Bipyridine (3.2 mmol) was dissolved in ethanol (25 ml) and perchloric acid (3.2 mmol) was then added dropwise. The reaction mixture was warmed in a water bath for 15 min and colourless crystals of (I) separated out on cooling (m.p. 441 K).

Crystal data

C₁₀H₉N₂⁺·ClO₄⁻
M_r = 256.64
Monoclinic, P c
a = 5.958 (4) Å
b = 12.854 (4) Å
c = 7.060 (11) Å
β = 100.26 (7)°
V = 532.0 (9) Å³
Z = 2
D_x = 1.602 Mg m⁻³
Mo Kα radiation
Cell parameters from 2313 reflections
θ = 3.2–27.5°
μ = 0.36 mm⁻¹
T = 120 (2) K
Plate, colourless
0.18 × 0.12 × 0.02 mm

Data collection

Bruker–Nonius KappaCCD area-detector diffractometer
φ and ω scans
Absorption correction: multi-scan(SADABS; Sheldrick, 2003 )T_min = 0.954, T_max = 0.993
6904 measured reflections
2313 independent reflections
2035 reflections with I > 2σ(I)
R_int = 0.046
θ_max = 27.5°
h = −7 → 7
k = −16 → 16
l = −9 → 9

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.115
S = 1.07
2313 reflections
155 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0712P)² + 0.011P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.46 e Å⁻³
Absolute structure: Flack (1983 ), with 1086 Friedel pairs
Flack parameter: 0.03 (16)

Table 1
Selected geometric parameters (Å, °)

Cl1—O1	1.452 (3)
Cl1—O2	1.433 (2)
Cl1—O3	1.439 (2)
Cl1—O4	1.438 (3)

C12—N11—C16	123.3 (3)
C22—N21—C26	117.0 (2)

N11—C12—C22—N21	−14.6 (4)
N11—C12—C22—C23	166.0 (3)
C13—C12—C22—N21	164.1 (3)
C13—C12—C22—C23	−15.3 (4)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N11—H11⋯O1	0.88	2.11	2.902 (6)	150
C13—H13⋯O4ⁱ	0.95	2.51	3.328 (7)	144
C14—H14⋯O3ⁱⁱ	0.95	2.57	3.375 (7)	142
C15—H15⋯O2ⁱⁱ	0.95	2.57	3.365 (6)	141
C16—H16⋯O3	0.95	2.52	3.289 (6)	139
Symmetry codes: (i) x-1, y, z+1; (ii) $[x-1, -y, z+{\script{1\over 2}}]$ .

The systematic absences permitted Pc and P2/c as possible space groups; Pc was selected and confirmed by the subsequent analysis. All H atoms were located in difference maps and then treated as riding atoms, with C—H distances of 0.95 Å and N—H distances of 0.88 Å, and with U_iso(H) = 1.2U_eq(C,N). The correct orientation of the structure with respect to the polar-axis directions (Jones, 1986 ) was determined by means of the Flack (1983) parameter.

Data collection: COLLECT (Hooft, 1999 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: OSCAIL (McArdle, 2003 ) and SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S0108270105018810/sk1853sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S0108270105018810/sk1853Isup2.hkl

Comment top

The structure of the title compound, (I), was determined many years ago (Lipkowski et al., 1976); using diffraction data collected at ambient temperature, the structure was refined only to R = 0.072. We have now redetermined this structure using diffraction data collected at 120 K, and we report here a more precise determination, together with the interesting supramolecular structure of this compound. The space group and unit-cell dimensions confirm that the previous study and the present work involve the same phase.

The title compound (Fig. 1) is a salt, and in the selected asymmetric unit, the two ions are linked by an N—H···O hydrogen bond. In the cation, the dihedral angle between the two ring planes is 14.96 (15)°, similar to the 16.6° reported earlier for the ambient-temperature structure (Lipkowski et al., 1976). In addition, there is a significant difference in the C—N—C angles at the protonated atom N11 and the unprotonated atom N21 (Table 1). In the anion, the Cl—O distance involving atom O1 is somewhat longer than the other Cl—O distances, possibly reflecting some modest localization of the negative charge.

In addition to the N—H···O hydrogen bond, involving the more negative atom O1 as the acceptor, there are a number of independent C—H···O hydrogen bonds (Table 2). Although these all have fairly long H···O distances, they all appear to have some structural significance, including the effective tethering of the perchlorate anion, for which the anisotropic displacement parameters give no indication of significant libration, far less of the type of disorder for which this anion is notorious. Hence we conclude that these interactions are significant. All of the hydrogen bonds involve donors in the protonated pyridinium ring, leading to more acidic X—H bonds (X = C or N), and all four O atoms of the anion act as acceptors, so precluding any significant librational motion for the anion.

The C—H···O hydrogen bond involving atom C16 as the donor reinforces the N—H···O hydrogen bond in linking together the two independent ions, so forming an R₂²(7) motif, and the combination of this and the interaction having atom C13 as the donor then generates by translation a C₂²(8)C₂²(9)[R₂²(7)] chain of rings running parallel to the [101] direction (Fig. 2). The two hydrogen bonds having atoms C14 and C15 as the donors act cooperatively to form a zigzag chain of edge-fused rings running parallel to the [201] direction and generated by the c-glide plane at y = 0 (Fig. 3). The combination of the [101] and [201] chains then generates a complex (010) sheet.

Experimental top

2,2'-Bipyridine (3.2 mmol) was dissolved in ethanol (Volume?) and perchloric acid (3.2 mmol) was then added dropwise. The reaction mixture was warmed in a water bath for 15 min and colourless crystals of (I) suitable for single-crystal X-ray diffraction separated out on cooling (m.p. 441 K).

Computing details top

Data collection: COLLECT (Hooft, 1999); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

Figures top

	Fig. 1. The independent components of compound (I), showing the atom-labelling scheme and the N—H···O hydrogen bond (dashed line). Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. Part of the crystal structure of (I), showing the formation of a hydrogen-bonded chain of rings along [101]. For the sake of clarity, the H atoms not involved in the motif shown have been omitted. The atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (x − 1, y, 1 + z) and (1 + x, y, z − 1), respectively.
	Fig. 3. Part of the crystal structure of (I), showing the formation of a hydrogen-bonded chains of rings along [201]. For the sake of clarity, the H atoms not involved in the motif shown have been omitted. The atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (x − 1, −y, 1/2 + z) and (1 + x, −y, z − 1/2), respectively.

2-(2-Pyridyl)pyridinium perchlorate top

Crystal data top

C₁₀H₉N₂⁺·ClO₄⁻	F(000) = 264
M_r = 256.64	D_x = 1.602 Mg m⁻³
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yc	Cell parameters from 2313 reflections
a = 5.958 (4) Å	θ = 3.2–27.5°
b = 12.854 (4) Å	µ = 0.36 mm⁻¹
c = 7.060 (11) Å	T = 120 K
β = 100.26 (7)°	Plate, colourless
V = 532.0 (9) Å³	0.18 × 0.12 × 0.02 mm
Z = 2

Data collection top

Bruker Nonius KappaCCD area-detector diffractometer	2313 independent reflections
Radiation source: Bruker-Nonius FR91 rotating anode	2035 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 3.2°
ϕ and ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −16→16
T_min = 0.954, T_max = 0.993	l = −9→9
6904 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.115	w = 1/[σ²(F_o²) + (0.0712P)² + 0.011P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
2313 reflections	Δρ_max = 0.46 e Å⁻³
155 parameters	Δρ_min = −0.46 e Å⁻³
2 restraints	Absolute structure: Flack (1983), with 1086 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.03 (16)

Crystal data top

C₁₀H₉N₂⁺·ClO₄⁻	V = 532.0 (9) Å³
M_r = 256.64	Z = 2
Monoclinic, Pc	Mo Kα radiation
a = 5.958 (4) Å	µ = 0.36 mm⁻¹
b = 12.854 (4) Å	T = 120 K
c = 7.060 (11) Å	0.18 × 0.12 × 0.02 mm
β = 100.26 (7)°

Data collection top

Bruker Nonius KappaCCD area-detector diffractometer	2313 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2035 reflections with I > 2σ(I)
T_min = 0.954, T_max = 0.993	R_int = 0.046
6904 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.115	Δρ_max = 0.46 e Å⁻³
S = 1.07	Δρ_min = −0.46 e Å⁻³
2313 reflections	Absolute structure: Flack (1983), with 1086 Friedel pairs
155 parameters	Absolute structure parameter: 0.03 (16)
2 restraints

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

	x	y	z	U_iso*/U_eq
Cl1	0.78153 (11)	0.18772 (5)	0.12569 (11)	0.02248 (19)
O1	0.7292 (4)	0.25897 (17)	0.2714 (3)	0.0264 (5)
O2	1.0236 (4)	0.18298 (16)	0.1357 (3)	0.0288 (5)
O3	0.6951 (4)	0.08604 (18)	0.1587 (4)	0.0432 (7)
O4	0.6765 (4)	0.2262 (2)	−0.0603 (3)	0.0397 (6)
N11	0.3950 (4)	0.21493 (19)	0.5136 (4)	0.0205 (5)
N21	0.4404 (4)	0.42048 (19)	0.5365 (4)	0.0221 (6)
C12	0.2347 (5)	0.2674 (2)	0.5864 (4)	0.0207 (6)
C13	0.0777 (5)	0.2114 (3)	0.6677 (5)	0.0244 (7)
C14	0.0897 (5)	0.1034 (3)	0.6715 (5)	0.0256 (7)
C15	0.2574 (6)	0.0523 (2)	0.5932 (5)	0.0277 (7)
C16	0.4097 (5)	0.1101 (2)	0.5145 (4)	0.0240 (7)
C22	0.2440 (5)	0.3824 (2)	0.5763 (4)	0.0200 (6)
C23	0.0631 (5)	0.4445 (2)	0.6077 (5)	0.0231 (6)
C24	0.0889 (5)	0.5522 (2)	0.6041 (5)	0.0247 (6)
C25	0.2908 (5)	0.5928 (2)	0.5643 (4)	0.0237 (6)
C26	0.4596 (5)	0.5242 (2)	0.5293 (5)	0.0241 (6)
H11	0.4954	0.2507	0.4627	0.025*
H13	−0.0373	0.2464	0.7205	0.029*
H14	−0.0170	0.0644	0.7277	0.031*
H15	0.2660	−0.0215	0.5945	0.033*
H16	0.5257	0.0767	0.4604	0.029*
H23	−0.0749	0.4143	0.6311	0.028*
H24	−0.0298	0.5969	0.6284	0.030*
H25	0.3136	0.6659	0.5609	0.028*
H26	0.5961	0.5525	0.4987	0.029*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0211 (3)	0.0219 (3)	0.0249 (4)	−0.0002 (3)	0.0053 (2)	−0.0006 (3)
O1	0.0290 (11)	0.0263 (12)	0.0264 (12)	0.0023 (8)	0.0116 (8)	−0.0028 (9)
O2	0.0180 (11)	0.0313 (13)	0.0376 (14)	0.0023 (8)	0.0066 (10)	0.0009 (9)
O3	0.0449 (15)	0.0218 (13)	0.068 (2)	−0.0139 (11)	0.0248 (14)	−0.0085 (12)
O4	0.0348 (14)	0.0613 (17)	0.0212 (13)	0.0141 (11)	0.0005 (10)	0.0028 (11)
N11	0.0211 (12)	0.0219 (12)	0.0187 (13)	−0.0006 (10)	0.0043 (10)	−0.0021 (10)
N21	0.0209 (12)	0.0234 (13)	0.0230 (14)	−0.0002 (10)	0.0069 (10)	−0.0016 (10)
C12	0.0166 (14)	0.0248 (15)	0.0202 (16)	0.0015 (11)	0.0019 (11)	−0.0005 (12)
C13	0.0209 (15)	0.0303 (16)	0.0224 (17)	0.0003 (12)	0.0045 (12)	0.0037 (13)
C14	0.0237 (15)	0.0268 (16)	0.0263 (17)	−0.0043 (12)	0.0042 (12)	0.0077 (13)
C15	0.0309 (17)	0.0239 (15)	0.0260 (19)	−0.0025 (13)	−0.0010 (14)	0.0017 (13)
C16	0.0298 (16)	0.0209 (15)	0.0204 (16)	0.0026 (11)	0.0018 (12)	0.0001 (12)
C22	0.0155 (13)	0.0259 (15)	0.0180 (16)	−0.0012 (10)	0.0010 (11)	−0.0007 (11)
C23	0.0202 (15)	0.0233 (15)	0.0257 (16)	0.0016 (11)	0.0043 (12)	−0.0022 (12)
C24	0.0245 (15)	0.0239 (16)	0.0244 (16)	0.0011 (12)	0.0005 (12)	−0.0022 (13)
C25	0.0233 (15)	0.0220 (15)	0.0233 (16)	0.0003 (11)	−0.0026 (13)	−0.0023 (11)
C26	0.0200 (13)	0.0283 (16)	0.0235 (15)	−0.0041 (12)	0.0028 (11)	−0.0014 (12)

Geometric parameters (Å, º) top

N11—C12	1.344 (4)	N21—C22	1.344 (4)
N11—C16	1.350 (4)	C22—C23	1.391 (4)
N11—H11	0.88	C23—C24	1.393 (4)
C12—C13	1.383 (4)	C23—H23	0.95
C12—C22	1.481 (4)	C24—C25	1.386 (4)
C13—C14	1.390 (4)	C24—H24	0.95
C13—H13	0.95	C25—C26	1.392 (4)
C14—C15	1.390 (5)	C25—H25	0.95
C14—H14	0.95	C26—H26	0.95
C15—C16	1.365 (5)	Cl1—O1	1.452 (3)
C15—H15	0.95	Cl1—O2	1.433 (2)
C16—H16	0.95	Cl1—O3	1.439 (2)
N21—C26	1.340 (4)	Cl1—O4	1.438 (3)

C12—N11—C16	123.3 (3)	N21—C22—C12	114.5 (2)
C12—N11—H11	118.4	C23—C22—C12	121.9 (2)
C16—N11—H11	118.4	C22—C23—C24	118.5 (3)
N11—C12—C13	118.5 (3)	C22—C23—H23	120.8
N11—C12—C22	116.6 (2)	C24—C23—H23	120.8
C13—C12—C22	125.0 (3)	C25—C24—C23	118.7 (3)
C12—C13—C14	119.5 (3)	C25—C24—H24	120.6
C12—C13—H13	120.3	C23—C24—H24	120.6
C14—C13—H13	120.3	C24—C25—C26	118.5 (3)
C13—C14—C15	120.2 (3)	C24—C25—H25	120.7
C13—C14—H14	119.9	C26—C25—H25	120.7
C15—C14—H14	119.9	N21—C26—C25	123.7 (3)
C16—C15—C14	118.8 (3)	N21—C26—H26	118.2
C16—C15—H15	120.6	C25—C26—H26	118.2
C14—C15—H15	120.6	O2—Cl1—O4	109.28 (16)
N11—C16—C15	119.9 (3)	O2—Cl1—O3	109.86 (15)
N11—C16—H16	120.1	O4—Cl1—O3	110.53 (18)
C15—C16—H16	120.1	O2—Cl1—O1	109.47 (15)
C22—N21—C26	117.0 (2)	O4—Cl1—O1	108.43 (16)
N21—C22—C23	123.5 (3)	O3—Cl1—O1	109.26 (16)

C16—N11—C12—C13	0.5 (4)	N11—C12—C22—N21	−14.6 (4)
C16—N11—C12—C22	179.3 (2)	N11—C12—C22—C23	166.0 (3)
N11—C12—C13—C14	−0.1 (4)	C13—C12—C22—N21	164.1 (3)
C22—C12—C13—C14	−178.8 (3)	C13—C12—C22—C23	−15.3 (4)
C12—C13—C14—C15	−0.4 (5)	N21—C22—C23—C24	−2.2 (5)
C13—C14—C15—C16	0.5 (5)	C12—C22—C23—C24	177.2 (3)
C12—N11—C16—C15	−0.4 (5)	C22—C23—C24—C25	1.7 (5)
C14—C15—C16—N11	−0.1 (4)	C23—C24—C25—C26	0.1 (4)
C26—N21—C22—C23	0.7 (4)	C22—N21—C26—C25	1.3 (4)
C26—N21—C22—C12	−178.7 (3)	C24—C25—C26—N21	−1.7 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O1	0.88	2.11	2.902 (6)	150
C13—H13···O4ⁱ	0.95	2.51	3.328 (7)	144
C14—H14···O3ⁱⁱ	0.95	2.57	3.375 (7)	142
C15—H15···O2ⁱⁱ	0.95	2.57	3.365 (6)	141
C16—H16···O3	0.95	2.52	3.289 (6)	139

Symmetry codes: (i) x−1, y, z+1; (ii) x−1, −y, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₀H₉N₂⁺·ClO₄⁻
M_r	256.64
Crystal system, space group	Monoclinic, Pc
Temperature (K)	120
a, b, c (Å)	5.958 (4), 12.854 (4), 7.060 (11)
β (°)	100.26 (7)
V (Å³)	532.0 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.36
Crystal size (mm)	0.18 × 0.12 × 0.02

Data collection
Diffractometer	Bruker Nonius KappaCCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.954, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	6904, 2313, 2035
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.115, 1.07
No. of reflections	2313
No. of parameters	155
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.46
Absolute structure	Flack (1983), with 1086 Friedel pairs
Absolute structure parameter	0.03 (16)

Computer programs: COLLECT (Hooft, 1999), DENZO (Otwinowski & Minor, 1997) and COLLECT, DENZO and COLLECT, OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997), OSCAIL and SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97 and PRPKAPPA (Ferguson, 1999).

Selected geometric parameters (Å, º) top

Cl1—O1	1.452 (3)	Cl1—O3	1.439 (2)
Cl1—O2	1.433 (2)	Cl1—O4	1.438 (3)

C12—N11—C16	123.3 (3)	C22—N21—C26	117.0 (2)

N11—C12—C22—N21	−14.6 (4)	C13—C12—C22—N21	164.1 (3)
N11—C12—C22—C23	166.0 (3)	C13—C12—C22—C23	−15.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O1	0.88	2.11	2.902 (6)	150
C13—H13···O4ⁱ	0.95	2.51	3.328 (7)	144
C14—H14···O3ⁱⁱ	0.95	2.57	3.375 (7)	142
C15—H15···O2ⁱⁱ	0.95	2.57	3.365 (6)	141
C16—H16···O3	0.95	2.52	3.289 (6)	139

Symmetry codes: (i) x−1, y, z+1; (ii) x−1, −y, z+1/2.

Acknowledgements

The X-ray data were collected at the EPSRC X-ray Crystallographic Service, University of Southampton, England; the authors thank the staff for all their help and advice.

References

Ferguson, G. (1999). PRPKAPPA. University of Guelph, Canada. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Hooft, R. W. W. (1999). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Jones, P. G. (1986). Acta Cryst. A42, 57. CrossRef Web of Science IUCr Journals Google Scholar
Lipkowski, J., Sgarabotto, P. & Andreetti, G. D. (1976). Cryst. Struct. Commun. 5, 931–934. CAS Google Scholar
McArdle, P. (2003). OSCAIL for Windows. Version 10. Crystallography Centre, Chemistry Department, NUI Galway, Ireland. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2003). SADABS. Version 2.10. University of Göttingen, Germany. Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2053-2296

Volume 61| Part 8| August 2005| Pages o473-o474

doi:10.1107/S0108270105018810

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

2-(2-Pyridyl)pyridinium perchlorate, redetermined at 120 K: complex hydrogen-bonded sheets

Comment

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds