Anilinium hydrogen sulfate.

The asymmetric unit of the title compound, C(6)H(8)N(+)·HSO(4) (-), contains two cations and two anions which are linked to each other through N-H⋯O hydrogen bonds, formed by all H atoms covalently bonded to the N atoms. In addition, strong O-H⋯O anion-anion hydrogen-bond inter-actions are also observed.

Related literature

For hydrogen bonding, see: Zimmerman & Corbin (2000 ▶); Brunsveld et al. (2001 ▶); Desiraju (2002 ▶); Desiraju & Steiner (1999 ▶); Steiner (2002 ▶); Etter et al. (1990 ▶); Bernstein et al. (1995 ▶). For related structures, see: Benali-Cherif, Boussekine et al. (2009 ▶); Messai et al. (2009 ▶); Benali-Cherif, Falek et al. (2009 ▶); Rademeyer (2004 ▶); Jayaraman et al. (2002 ▶); Smith et al. (2004 ▶); Paixão et al. (2000 ▶).

Experimental

Crystal data

C6H8N+·HSO4 −

M = 191.20

Orthorhombic,

a = 14.3201 (2) Å

b = 9.0891 (3) Å

c = 12.8771 (2) Å

V = 1676.04 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.36 mm−1

T = 293 K

0.2 × 0.15 × 0.1 mm

Data collection

Nonius KappaCCD diffractometer

16963 measured reflections

4641 independent reflections

3108 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.117

S = 1.02

4641 reflections

219 parameters

1 restraint

H-atom parameters not refined

Δρmax = 0.35 e Å−3

Δρmin = −0.47 e Å−3

Absolute structure: Flack (1983 ▶), 2096 Friedel pairs

Flack parameter: 0.08 (9)

Data collection: KappaCCD Server Software (Nonius, 1998 ▶); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-32 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I. DOI: 10.1107/S1600536810004782/dn2534sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810004782/dn2534Isup2.hkl

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

C6H8N+·HSO4−	F(000) = 800
Mr = 191.20	Dx = 1.516 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 16963 reflections
a = 14.3201 (2) Å	θ = 2.7–30.0°
b = 9.0891 (3) Å	µ = 0.36 mm−1
c = 12.8771 (2) Å	T = 293 K
V = 1676.04 (7) Å3	Prism, colourless
Z = 8	0.2 × 0.15 × 0.1 mm

Nonius KappaCCD diffractometer	3108 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.049
graphite	θmax = 30.0°, θmin = 2.7°
ω – θ scans	h = −19→17
16963 measured reflections	k = −9→12
4641 independent reflections	l = −18→16

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)] = 0.041	H-atom parameters not refined
wR(F2) = 0.117	w = 1/[σ2(Fo2) + (0.0622P)2 + 0.1354P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
4641 reflections	Δρmax = 0.35 e Å−3
219 parameters	Δρmin = −0.47 e Å−3
1 restraint	Absolute structure: Flack (1983), 2096 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.08 (9)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
N1A	0.21732 (15)	0.3085 (2)	0.3390 (2)	0.0432 (5)
H22	0.2392	0.3525	0.2823	0.065*
H33	0.2550	0.3273	0.3924	0.065*
H11	0.1603	0.3422	0.3530	0.065*
C1A	0.21307 (19)	0.1496 (3)	0.3217 (3)	0.0363 (7)
C2A	0.1721 (3)	0.0988 (4)	0.2311 (3)	0.0531 (8)
H2A	0.1482	0.1641	0.1823	0.064*
C3A	0.1676 (3)	−0.0512 (4)	0.2153 (3)	0.0626 (10)
H3A	0.1398	−0.0875	0.1553	0.075*
C4A	0.2039 (2)	−0.1480 (4)	0.2873 (4)	0.0640 (11)
H4A	0.2006	−0.2489	0.2760	0.077*
C5A	0.2449 (3)	−0.0940 (4)	0.3758 (3)	0.0555 (9)
H5A	0.2698	−0.1588	0.4243	0.067*
C6A	0.2493 (3)	0.0551 (4)	0.3931 (3)	0.0458 (7)
H6A	0.2770	0.0912	0.4533	0.055*
N1B	0.52868 (13)	0.2975 (2)	0.5035 (2)	0.0403 (5)
H1	0.5861	0.3342	0.4989	0.061*
H2	0.4989	0.3397	0.5564	0.061*
H3	0.4978	0.3154	0.4448	0.061*
C1B	0.53385 (18)	0.1390 (3)	0.5207 (2)	0.0330 (6)
C2B	0.5767 (2)	0.0855 (4)	0.6081 (3)	0.0498 (8)
H2B	0.6015	0.1493	0.6573	0.060*
C3B	0.5824 (3)	−0.0655 (4)	0.6217 (4)	0.0622 (10)
H3B	0.6104	−0.1037	0.6810	0.075*
C4B	0.5467 (3)	−0.1590 (4)	0.5479 (4)	0.0622 (11)
H4B	0.5521	−0.2602	0.5568	0.075*
C5B	0.5030 (3)	−0.1046 (4)	0.4610 (4)	0.0599 (11)
H5B	0.4775	−0.1685	0.4122	0.072*
C6B	0.4973 (3)	0.0456 (4)	0.4468 (3)	0.0453 (7)
H6B	0.4688	0.0836	0.3877	0.054*
S1A	0.47642 (6)	0.50293 (6)	0.27815 (5)	0.0354 (3)
O1A	0.53917 (14)	0.5609 (3)	0.3548 (2)	0.0588 (5)
O2A	0.43955 (15)	0.3610 (2)	0.30490 (17)	0.0501 (5)
O3A	0.5129 (3)	0.5072 (3)	0.1721 (3)	0.0610 (11)
O4A	0.39386 (13)	0.6139 (2)	0.27837 (19)	0.0492 (5)
H4	0.3495	0.5784	0.2468	0.074*
S1B	0.22562 (6)	0.50860 (7)	0.06533 (5)	0.0340 (3)
O1B	0.29288 (13)	0.5696 (2)	−0.00469 (18)	0.0543 (5)
O2B	0.18378 (13)	0.3739 (2)	0.02858 (18)	0.0477 (5)
O3B	0.2609 (3)	0.4930 (2)	0.1701 (3)	0.0570 (10)
O4B	0.14771 (13)	0.6268 (2)	0.0699 (2)	0.0493 (5)
H44	0.1067	0.6000	0.1100	0.074*

	U11	U22	U33	U12	U13	U23
N1A	0.0488 (13)	0.0354 (12)	0.0452 (12)	0.0039 (9)	−0.0019 (9)	−0.0050 (10)
C1A	0.0319 (14)	0.0339 (15)	0.0431 (16)	0.0026 (11)	0.0016 (12)	−0.0062 (12)
C2A	0.0594 (19)	0.0502 (19)	0.0496 (18)	0.0050 (16)	−0.0107 (17)	−0.0079 (17)
C3A	0.069 (2)	0.055 (2)	0.063 (3)	−0.001 (2)	−0.0126 (19)	−0.023 (2)
C4A	0.0542 (19)	0.0386 (19)	0.099 (3)	−0.0010 (14)	0.007 (2)	−0.022 (2)
C5A	0.0558 (18)	0.0426 (17)	0.068 (3)	0.0087 (16)	−0.0002 (19)	0.0097 (17)
C6A	0.0451 (15)	0.045 (2)	0.0471 (18)	−0.0003 (18)	−0.0043 (14)	−0.0026 (16)
N1B	0.0429 (11)	0.0348 (12)	0.0433 (11)	−0.0024 (9)	0.0007 (9)	−0.0008 (10)
C1B	0.0320 (14)	0.0303 (14)	0.0366 (15)	−0.0033 (10)	0.0044 (11)	0.0006 (11)
C2B	0.0532 (18)	0.0478 (18)	0.0483 (17)	0.0025 (15)	−0.0088 (16)	0.0018 (15)
C3B	0.062 (2)	0.058 (3)	0.067 (2)	0.008 (2)	0.003 (2)	0.024 (2)
C4B	0.0561 (19)	0.0345 (18)	0.096 (3)	−0.0007 (15)	0.021 (2)	0.0099 (19)
C5B	0.0511 (18)	0.045 (2)	0.084 (3)	−0.0072 (17)	0.004 (2)	−0.0201 (19)
C6B	0.0410 (15)	0.0461 (19)	0.0487 (19)	−0.0017 (18)	−0.0040 (14)	−0.0100 (17)
S1A	0.0319 (6)	0.0352 (5)	0.0392 (6)	−0.0012 (2)	−0.0005 (5)	0.0038 (2)
O1A	0.0503 (12)	0.0554 (14)	0.0705 (14)	−0.0116 (11)	−0.0226 (10)	0.0051 (12)
O2A	0.0625 (13)	0.0365 (11)	0.0514 (12)	−0.0065 (10)	−0.0036 (10)	0.0067 (8)
O3A	0.058 (2)	0.075 (2)	0.050 (2)	0.0183 (11)	0.0188 (19)	0.0205 (10)
O4A	0.0391 (10)	0.0430 (11)	0.0655 (13)	0.0065 (8)	−0.0047 (9)	−0.0081 (10)
S1B	0.0305 (6)	0.0341 (5)	0.0374 (5)	−0.0020 (2)	0.0013 (4)	−0.0020 (3)
O1B	0.0427 (11)	0.0621 (16)	0.0580 (13)	−0.0112 (10)	0.0141 (9)	0.0022 (12)
O2B	0.0499 (11)	0.0368 (10)	0.0564 (12)	−0.0074 (9)	0.0048 (9)	−0.0099 (9)
O3B	0.0476 (18)	0.073 (2)	0.050 (2)	−0.0086 (10)	−0.0119 (18)	0.0084 (10)
O4B	0.0470 (11)	0.0379 (11)	0.0630 (12)	0.0054 (9)	0.0082 (10)	0.0013 (10)

N1A—C1A	1.462 (4)	C1B—C6B	1.378 (4)
N1A—H22	0.8900	C2B—C3B	1.386 (6)
N1A—H33	0.8900	C2B—H2B	0.9300
N1A—H11	0.8900	C3B—C4B	1.373 (6)
C1A—C6A	1.361 (5)	C3B—H3B	0.9300
C1A—C2A	1.385 (5)	C4B—C5B	1.374 (6)
C2A—C3A	1.380 (5)	C4B—H4B	0.9300
C2A—H2A	0.9300	C5B—C6B	1.380 (4)
C3A—C4A	1.380 (6)	C5B—H5B	0.9300
C3A—H3A	0.9300	C6B—H6B	0.9300
C4A—C5A	1.372 (6)	S1A—O1A	1.435 (2)
C4A—H4A	0.9300	S1A—O2A	1.436 (2)
C5A—C6A	1.375 (4)	S1A—O3A	1.463 (4)
C5A—H5A	0.9300	S1A—O4A	1.554 (2)
C6A—H6A	0.9300	O4A—H4	0.8201
N1B—C1B	1.460 (3)	S1B—O1B	1.431 (2)
N1B—H1	0.8900	S1B—O2B	1.4430 (19)
N1B—H2	0.8900	S1B—O3B	1.448 (4)
N1B—H3	0.8900	S1B—O4B	1.550 (2)
C1B—C2B	1.371 (4)	O4B—H44	0.8200
C1A—N1A—H22	109.5	C2B—C1B—N1B	119.8 (3)
C1A—N1A—H33	109.5	C6B—C1B—N1B	119.0 (3)
H22—N1A—H33	109.5	C1B—C2B—C3B	118.8 (3)
C1A—N1A—H11	109.5	C1B—C2B—H2B	120.6
H22—N1A—H11	109.5	C3B—C2B—H2B	120.6
H33—N1A—H11	109.5	C4B—C3B—C2B	120.2 (3)
C6A—C1A—C2A	121.4 (3)	C4B—C3B—H3B	119.9
C6A—C1A—N1A	120.3 (3)	C2B—C3B—H3B	119.9
C2A—C1A—N1A	118.4 (3)	C3B—C4B—C5B	120.7 (4)
C3A—C2A—C1A	118.2 (3)	C3B—C4B—H4B	119.7
C3A—C2A—H2A	120.9	C5B—C4B—H4B	119.7
C1A—C2A—H2A	120.9	C4B—C5B—C6B	119.4 (3)
C2A—C3A—C4A	120.9 (3)	C4B—C5B—H5B	120.3
C2A—C3A—H3A	119.6	C6B—C5B—H5B	120.3
C4A—C3A—H3A	119.6	C1B—C6B—C5B	119.7 (3)
C5A—C4A—C3A	119.4 (3)	C1B—C6B—H6B	120.2
C5A—C4A—H4A	120.3	C5B—C6B—H6B	120.2
C3A—C4A—H4A	120.3	O1A—S1A—O2A	113.28 (16)
C4A—C5A—C6A	120.5 (3)	O1A—S1A—O3A	114.1 (2)
C4A—C5A—H5A	119.8	O2A—S1A—O3A	112.27 (15)
C6A—C5A—H5A	119.8	O1A—S1A—O4A	103.72 (14)
C1A—C6A—C5A	119.6 (3)	O2A—S1A—O4A	107.62 (12)
C1A—C6A—H6A	120.2	O3A—S1A—O4A	104.85 (16)
C5A—C6A—H6A	120.2	S1A—O4A—H4	109.5
C1B—N1B—H1	109.5	O1B—S1B—O2B	113.68 (16)
C1B—N1B—H2	109.5	O1B—S1B—O3B	113.0 (2)
H1—N1B—H2	109.5	O2B—S1B—O3B	111.55 (14)
C1B—N1B—H3	109.5	O1B—S1B—O4B	103.86 (13)
H1—N1B—H3	109.5	O2B—S1B—O4B	107.56 (12)
H2—N1B—H3	109.5	O3B—S1B—O4B	106.47 (17)
C2B—C1B—C6B	121.2 (3)	S1B—O4B—H44	109.5
C6A—C1A—C2A—C3A	0.9 (5)	C6B—C1B—C2B—C3B	−0.4 (4)
N1A—C1A—C2A—C3A	−179.6 (3)	N1B—C1B—C2B—C3B	−178.8 (3)
C1A—C2A—C3A—C4A	−0.7 (5)	C1B—C2B—C3B—C4B	0.9 (4)
C2A—C3A—C4A—C5A	0.0 (6)	C2B—C3B—C4B—C5B	−1.6 (5)
C3A—C4A—C5A—C6A	0.4 (6)	C3B—C4B—C5B—C6B	1.7 (6)
C2A—C1A—C6A—C5A	−0.4 (5)	C2B—C1B—C6B—C5B	0.5 (5)
N1A—C1A—C6A—C5A	−180.0 (3)	N1B—C1B—C6B—C5B	178.9 (3)
C4A—C5A—C6A—C1A	−0.2 (5)	C4B—C5B—C6B—C1B	−1.1 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H11···O1Ai	0.89	1.95	2.821 (2)	167
N1B—H2···O3Aii	0.89	2.05	2.867 (3)	153
N1A—H33···O2Biii	0.89	2.01	2.884 (3)	169
N1B—H3···O1A	0.89	2.58	3.069 (3)	115
N1B—H3···O2A	0.89	2.03	2.916 (3)	175
N1A—H22···O3B	0.89	1.95	2.817 (4)	163
O4A—H4···O3B	0.82	1.79	2.603 (4)	175
O4B—H44···O3Ai	0.82	1.84	2.635 (4)	163
N1B—H1···O1Bii	0.89	1.94	2.828 (3)	175

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H11⋯O1Ai	0.89	1.95	2.821 (2)	167
N1A—H22⋯O3B	0.89	1.95	2.817 (4)	163
N1A—H33⋯O2Biii	0.89	2.01	2.884 (3)	169
N1B—H1⋯O1Bii	0.89	1.94	2.828 (3)	175
N1B—H2⋯O3Aii	0.89	2.05	2.867 (3)	153
N1B—H3⋯O1A	0.89	2.58	3.069 (3)	115
N1B—H3⋯O2A	0.89	2.03	2.916 (3)	175
O4A—H4⋯O3B	0.82	1.79	2.603 (4)	175
O4B—H44⋯O3Ai	0.82	1.84	2.635 (4)	163

Symmetry codes: (i) ; (ii) ; (iii) .