4-Benzyl­pyridinium hydrogen selenate

Maalej, W.; Elaoud, Z.; Mhiri, T.; Daoud, A.; Driss, A.

doi:10.1107/S1600536808033801

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2172

doi:10.1107/S1600536808033801

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4-Benzylpyridinium hydrogen selenate

Wassim Maalej,^a ^* Zakaria Elaoud,^a Tahar Mhiri,^a Abdelaziz Daoud ^a and Ahmed Driss ^b

^aLaboratoire de l'Etat Solide, Faculté des Sciences de Sfax, BP 1171, 3000 Sfax, Tunisia, and ^bLaboratoire de Matériaux et Cristallochimie, Département de Chimie, Faculté des Sciences, 2092 Campus Universitaire, Tunis, Tunisia
^*Correspondence e-mail: maalej_wassim@yahoo.fr

(Received 15 April 2008; accepted 16 October 2008; online 22 October 2008)

The structure of the title salt, C₁₂H₁₂N⁺·HSeO₄⁻, consists of infinite parallel two-dimensional planes built of 4-benzylpyridinium and hydrogen selenate ions that are mutually connected by strong O—H⋯O and N—H⋯O hydrogen bonds. There are no contacts other than normal van der Waals interactions between the layers.

Related literature

For general background, see Fleck (2006 ); Baran et al. (2000 ). For related compounds, see: Ben Hamada & Jouini (2006 ); Kaabi et al. (2004 ); Ben Djemaa et al. (2007 ); Gowda et al. (2007 ).

Experimental

Crystal data

C₁₂H₁₂N⁺·HSeO₄⁻
M_r = 314.19
Orthorhombic, P b c a
a = 27.449 (5) Å
b = 10.821 (6) Å
c = 8.830 (1) Å
V = 2623 (2) Å³
Z = 8
Mo Kα radiation
μ = 2.87 mm⁻¹
T = 289 (2) K
0.11 × 0.09 × 0.04 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.743, T_max = 0.894
3179 measured reflections
2817 independent reflections
1486 reflections with I > 2σ(I)
R_int = 0.045
2 standard reflections frequency: 120 min intensity decay: 11%

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.087
S = 0.98
2817 reflections
207 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—HO3⋯O4ⁱ	0.82	1.89	2.617 (4)	148
N—HN⋯O2ⁱⁱ	0.95 (4)	1.82 (5)	2.762 (5)	168 (4)
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ) and DIAMOND (Brandenburg, 1998 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808033801/im2065sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808033801/im2065Isup2.hkl

checkCIF report

Comment top

The title compound C₆H₅CH₂C₅H₄NH⁺ HSeO₄^- crystallizes in the orthorhombic space group Pbca. Correspondingly, there are eight formula units per unit cell. The crystal is built up of monohydrogenselenate anions connected by hydrogen bonds of the O—H···O type forming infinite chains [HSeO₄]_n^n- perpendicular to the [001] directions.

These chains are themselves interconnected by means of N—H···O hydrogen bonds originating from the [C₆H₅CH₂C₅H₄NH]⁺ cation, so as to build a three-dimensional network. The distances Se—O in the [HSeO₄]^- anions range from 1.608 (3) to 1.705 (3) Å (Fig. 1). These values are comparable to reported data (Fleck, 2006). The longest Se—O(2) distance of 1.705 (3) Å, is due to the presence of the acidic hydrogen atom on the SeO₄ tetrahedron (Baran et al., 2000).

The organic groups are located in the (011) planes at x = 1/4 and x = 3/4. The average values of the C—C, C—N and C═C bond lengths of 1.5165 (6) Å, 1.3305 (6) Å and 1.3753 (6) Å in the [C₆H₅CH₂C₅H₄NH]⁺ cation are similar to those observed in related compounds (Ben Hamada & Jouini, 2006; Kaabi et al., 2004; Ben Djemaa et al., 2007; Gowda et al., 2007). The C—C perpendicular interplanar distances range from 1.74 to 4.83 Å and the dihedral angle between two planes of rings is 67.04°, indicating the existence of strong van der Waals interactions by contacts between [C₆H₅CH₂C₅H₄NH]⁺ cations.

All the hydrogen bonds (D—H···O, Table 1) and the van der Waals contacts give rise to a three dimensional network in the crystal structure.

Related literature top

For related literature, see Fleck (2006); Baran et al. (2000); Ben Hamada & Jouini (2006); Kaabi et al. (2004); Ben Djemaa et al. (2007); Gowda et al. (2007).

Experimental top

Crystals of the title compound C₆H₅CH₂C₅H₄NH⁺ HSeO₄^- were prepared by slowly adding, at room temperature, an equimolecular proportion of H₂SeO₄ (1.9 cm³) to a solution of 4-benzyl pyridine (5 cm³). A crystalline precipitate was formed. After dissolving the precipitate by adding H₂O, the solution is allowed to slowly evaporate at room temperature for several days until the formation of pink prismatic crystals with dimensions suitable for a crystallographic study occurs.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. ORTEP drawing of [C₆H₅CH₂C₅H₄NH]⁺ [HSeO₄]^-.
	Fig. 2. Projection along the b axis of the crystal structure of [C₆H₅CH₂C₅H₄NH]⁺ [HSeO₄]^-.

4-Benzylpyridinium hydrogen selenate top

Crystal data top

C₁₂H₁₂N⁺·HSeO₄⁻	F(000) = 1264
M_r = 314.19	D_x = 1.592 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 25 reflections
a = 27.449 (5) Å	θ = 14–16°
b = 10.821 (6) Å	µ = 2.87 mm⁻¹
c = 8.830 (1) Å	T = 289 K
V = 2623 (2) Å³	Prism, pink
Z = 8	0.11 × 0.09 × 0.04 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1486 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.045
Graphite monochromator	θ_max = 27.0°, θ_min = 2.4°
Non–profiled ω/2θ scans	h = 0→35
Absorption correction: ψ scan (North et al., 1968)	k = 0→13
T_min = 0.743, T_max = 0.894	l = −2→11
3179 measured reflections	2 standard reflections every 120 min
2817 independent reflections	intensity decay: 11%

Refinement top

Refinement on F²	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.0299P)²] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.037	(Δ/σ)_max = 0.001
wR(F²) = 0.087	Δρ_max = 0.28 e Å⁻³
S = 0.98	Δρ_min = −0.31 e Å⁻³
2817 reflections	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
207 parameters	Extinction coefficient: 0.0065 (3)
0 restraints

Crystal data top

C₁₂H₁₂N⁺·HSeO₄⁻	V = 2623 (2) Å³
M_r = 314.19	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 27.449 (5) Å	µ = 2.87 mm⁻¹
b = 10.821 (6) Å	T = 289 K
c = 8.830 (1) Å	0.11 × 0.09 × 0.04 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1486 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.045
T_min = 0.743, T_max = 0.894	2 standard reflections every 120 min
3179 measured reflections	intensity decay: 11%
2817 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.087	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	Δρ_max = 0.28 e Å⁻³
2817 reflections	Δρ_min = −0.31 e Å⁻³
207 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
Se	0.568598 (14)	0.68653 (3)	0.34450 (4)	0.04502 (15)
O1	0.53870 (10)	0.8139 (2)	0.3574 (4)	0.0652 (8)
O2	0.53625 (10)	0.5754 (2)	0.2732 (4)	0.0685 (9)
O3	0.61665 (10)	0.7080 (3)	0.2250 (4)	0.0779 (10)
HO3	0.6065	0.7281	0.1411	0.11 (2)*
O4	0.59571 (11)	0.6441 (3)	0.4996 (3)	0.0644 (8)
C1	0.22067 (18)	0.5917 (5)	0.6315 (6)	0.0675 (14)
C2	0.21967 (19)	0.6932 (5)	0.5412 (7)	0.0746 (15)
C3	0.25920 (19)	0.7237 (5)	0.4540 (6)	0.0624 (13)
C4	0.30049 (14)	0.6492 (4)	0.4530 (4)	0.0460 (10)
C5	0.30108 (17)	0.5471 (4)	0.5468 (6)	0.0564 (12)
C6	0.26129 (17)	0.5184 (4)	0.6359 (6)	0.0681 (14)
HC6	0.2621	0.4494	0.6988	0.061 (13)*
C7	0.3437 (2)	0.6798 (6)	0.3529 (6)	0.0683 (14)
C8	0.38461 (14)	0.7417 (4)	0.4400 (4)	0.0462 (10)
C9	0.38853 (17)	0.8693 (4)	0.4482 (5)	0.0538 (11)
HC9	0.3662	0.9193	0.3977	0.046 (11)*
C10	0.42554 (19)	0.9215 (5)	0.5313 (6)	0.0630 (13)
C11	0.45454 (18)	0.7264 (5)	0.5991 (6)	0.0631 (13)
C12	0.41870 (17)	0.6719 (5)	0.5168 (6)	0.0580 (12)
N	0.45683 (14)	0.8484 (4)	0.6053 (5)	0.0621 (11)
HC1	0.1926 (15)	0.573 (4)	0.690 (5)	0.077 (15)*
HC2	0.1914 (18)	0.742 (5)	0.540 (6)	0.102 (18)*
HC3	0.2621 (16)	0.795 (4)	0.388 (5)	0.082 (16)*
HC5	0.3276 (13)	0.498 (4)	0.547 (4)	0.058 (13)*
H1C7	0.334 (2)	0.729 (6)	0.280 (7)	0.12 (2)*
H2C7	0.3573 (13)	0.602 (4)	0.309 (4)	0.062 (14)*
HC10	0.4295 (16)	1.006 (4)	0.543 (5)	0.090 (17)*
HC11	0.4786 (18)	0.680 (4)	0.661 (6)	0.104 (19)*
HC12	0.4167 (16)	0.587 (5)	0.503 (5)	0.087 (16)*
HN	0.4820 (15)	0.885 (4)	0.664 (5)	0.071 (14)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Se	0.0483 (2)	0.0418 (2)	0.0450 (2)	0.00559 (19)	0.0005 (2)	−0.0042 (2)
O1	0.0665 (18)	0.0466 (16)	0.082 (2)	0.0135 (15)	−0.0004 (18)	−0.0093 (17)
O2	0.0725 (19)	0.0479 (17)	0.085 (2)	0.0001 (16)	−0.0203 (18)	−0.0108 (17)
O3	0.0505 (17)	0.120 (3)	0.063 (2)	0.0120 (19)	0.0084 (16)	0.027 (2)
O4	0.093 (2)	0.0568 (17)	0.0429 (16)	0.0089 (17)	−0.0115 (16)	−0.0017 (15)
C1	0.057 (3)	0.070 (3)	0.075 (4)	−0.022 (3)	0.012 (3)	−0.016 (3)
C2	0.054 (3)	0.075 (4)	0.095 (4)	0.005 (3)	−0.007 (3)	−0.004 (4)
C3	0.075 (3)	0.055 (3)	0.057 (3)	−0.002 (3)	−0.013 (3)	0.008 (2)
C4	0.053 (3)	0.048 (2)	0.037 (2)	−0.019 (2)	0.001 (2)	−0.0074 (19)
C5	0.055 (3)	0.046 (3)	0.068 (3)	−0.001 (2)	0.007 (3)	0.001 (2)
C6	0.084 (4)	0.045 (3)	0.076 (4)	−0.013 (2)	0.016 (3)	0.013 (3)
C7	0.077 (3)	0.081 (4)	0.047 (3)	−0.028 (3)	0.010 (3)	−0.014 (3)
C8	0.053 (2)	0.050 (2)	0.036 (2)	−0.012 (2)	0.011 (2)	0.002 (2)
C9	0.060 (3)	0.051 (2)	0.050 (3)	−0.001 (2)	0.002 (2)	0.014 (2)
C10	0.072 (3)	0.051 (3)	0.066 (3)	−0.016 (3)	0.014 (3)	−0.006 (3)
C11	0.055 (3)	0.064 (3)	0.071 (3)	−0.006 (3)	0.008 (3)	0.020 (3)
C12	0.062 (3)	0.047 (3)	0.066 (3)	−0.009 (2)	0.011 (2)	0.005 (3)
N	0.045 (2)	0.082 (3)	0.059 (3)	−0.025 (2)	0.0041 (19)	0.000 (2)

Geometric parameters (Å, º) top

Se—O1	1.608 (3)	C6—HC6	0.93
Se—O2	1.622 (3)	C7—C8	1.518 (6)
Se—O4	1.625 (3)	C7—H1C7	0.88 (6)
Se—O3	1.705 (3)	C7—H2C7	1.00 (4)
O3—HO3	0.82	C8—C12	1.381 (6)
C1—C2	1.358 (7)	C8—C9	1.387 (6)
C1—C6	1.369 (7)	C9—C10	1.375 (6)
C1—HC1	0.95 (4)	C9—HC9	0.93
C2—C3	1.371 (7)	C10—N	1.338 (6)
C2—HC2	0.94 (5)	C10—HC10	0.93 (5)
C3—C4	1.391 (6)	C11—N	1.323 (6)
C3—HC3	0.97 (4)	C11—C12	1.358 (7)
C4—C5	1.381 (6)	C11—HC11	1.00 (5)
C4—C7	1.515 (6)	C12—HC12	0.93 (5)
C5—C6	1.382 (6)	N—HN	0.95 (4)
C5—HC5	0.90 (4)

O1—Se—O2	112.56 (15)	C4—C7—C8	112.4 (4)
O1—Se—O4	114.59 (15)	C4—C7—H1C7	109 (4)
O2—Se—O4	111.61 (15)	C8—C7—H1C7	109 (4)
O1—Se—O3	108.78 (16)	C4—C7—H2C7	109 (2)
O2—Se—O3	106.51 (16)	C8—C7—H2C7	107 (2)
O4—Se—O3	101.89 (16)	H1C7—C7—H2C7	110 (5)
Se—O3—HO3	109.5	C12—C8—C9	117.8 (4)
C2—C1—C6	120.1 (5)	C12—C8—C7	120.6 (4)
C2—C1—HC1	118 (3)	C9—C8—C7	121.5 (5)
C6—C1—HC1	122 (3)	C10—C9—C8	119.6 (4)
C1—C2—C3	120.6 (5)	C10—C9—HC9	120.2
C1—C2—HC2	119 (3)	C8—C9—HC9	120.2
C3—C2—HC2	121 (3)	N—C10—C9	119.5 (4)
C2—C3—C4	120.6 (5)	N—C10—HC10	117 (3)
C2—C3—HC3	126 (3)	C9—C10—HC10	123 (3)
C4—C3—HC3	113 (3)	N—C11—C12	119.3 (5)
C5—C4—C3	118.0 (4)	N—C11—HC11	117 (3)
C5—C4—C7	121.0 (4)	C12—C11—HC11	124 (3)
C3—C4—C7	121.0 (5)	C11—C12—C8	121.1 (5)
C4—C5—C6	120.8 (4)	C11—C12—HC12	123 (3)
C4—C5—HC5	119 (3)	C8—C12—HC12	116 (3)
C6—C5—HC5	121 (3)	C11—N—C10	122.6 (5)
C1—C6—C5	119.8 (5)	C11—N—HN	118 (3)
C1—C6—HC6	120.1	C10—N—HN	119 (3)
C5—C6—HC6	120.1

C6—C1—C2—C3	−0.2 (8)	C4—C7—C8—C12	85.0 (6)
C1—C2—C3—C4	2.0 (8)	C4—C7—C8—C9	−93.6 (6)
C2—C3—C4—C5	−2.6 (7)	C12—C8—C9—C10	−0.1 (6)
C2—C3—C4—C7	177.9 (4)	C7—C8—C9—C10	178.5 (4)
C3—C4—C5—C6	1.6 (7)	C8—C9—C10—N	−1.1 (6)
C7—C4—C5—C6	−178.9 (4)	N—C11—C12—C8	−0.2 (7)
C2—C1—C6—C5	−0.8 (8)	C9—C8—C12—C11	0.8 (6)
C4—C5—C6—C1	0.0 (7)	C7—C8—C12—C11	−177.8 (4)
C5—C4—C7—C8	−78.7 (6)	C12—C11—N—C10	−1.1 (7)
C3—C4—C7—C8	100.8 (6)	C9—C10—N—C11	1.8 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—HO3···O4ⁱ	0.82	1.89	2.617 (4)	148
N—HN···O2ⁱⁱ	0.95 (4)	1.82 (5)	2.762 (5)	168 (4)

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₂N⁺·HSeO₄⁻
M_r	314.19
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	289
a, b, c (Å)	27.449 (5), 10.821 (6), 8.830 (1)
V (Å³)	2623 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	2.87
Crystal size (mm)	0.11 × 0.09 × 0.04

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.743, 0.894
No. of measured, independent and observed [I > 2σ(I)] reflections	3179, 2817, 1486
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.638

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.087, 0.98
No. of reflections	2817
No. of parameters	207
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.31

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996) and DIAMOND (Brandenburg, 1998), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—HO3···O4ⁱ	0.82	1.89	2.617 (4)	147.8
N—HN···O2ⁱⁱ	0.95 (4)	1.82 (5)	2.762 (5)	168 (4)

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x, −y+3/2, z+1/2.

References

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2172

doi:10.1107/S1600536808033801

Open

access