4-Benzyl-pyridinium hydrogen selenate.

The structure of the title salt, C(12)H(12)N(+)·HSeO(4) (-), consists of infinite parallel two-dimensional planes built of 4-benzyl-pyridinium 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 inter-actions 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 = 314.19

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.087

S = 0.98

2817 reflections

207 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.31 e Å−3

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 ▶).

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C12H12N+·HSeO4−	F(000) = 1264
Mr = 314.19	Dx = 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

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

Refinement on F2	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0299P)2] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.037	(Δ/σ)max = 0.001
wR(F2) = 0.087	Δρmax = 0.28 e Å−3
S = 0.98	Δρmin = −0.30 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

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
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)*

	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)

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)

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)

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) ; (ii) .