Anilinium hydrogen sulfate

Boutobba, Z.; Direm, A.; Benali-Cherif, N.

doi:10.1107/S1600536810004782

organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Pages o595-o596

doi:10.1107/S1600536810004782

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Anilinium hydrogen sulfate

Zina Boutobba,^a Amani Direm ^a and Nourredine Benali-Cherif ^a ^*

^aLaboratoire des Structures, Propriétés et Interactions Inter-Atomiques., Centre Universitaire Abbes Laghrour, Khenchela 40000, Algeria
^*Correspondence e-mail: benalicherif@hotmail.com

(Received 23 January 2010; accepted 6 February 2010; online 13 February 2010)

The asymmetric unit of the title compound, C₆H₈N⁺·HSO₄⁻, 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 interactions 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_r = 191.20
Orthorhombic, P c a 2₁
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[F² > 2σ(F²)] = 0.041
wR(F²) = 0.117
S = 1.02
4641 reflections
219 parameters
1 restraint
H-atom parameters not refined
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.47 e Å⁻³
Absolute structure: Flack (1983 ), 2096 Friedel pairs
Flack parameter: 0.08 (9)

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) $[x-{\script{1\over 2}}, -y+1, z]$ ; (ii) $[-x+1, -y+1, z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, y, z+{\script{1\over 2}}]$ .

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 ).

Supporting information

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

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

checkCIF report

Comment top

The main purpose of this structural study was a determination of the arrangement of the cations and anions which are held together by two-dimensional hydrogen-bond networks.

Hydrogen bonding is one of the most versatile noncovalent forces in supramolecular chemistry and crystal engineering (Zimmerman & Corbin, 2000; Brunsveld et al., 2001; Desiraju, 2002). Therefore, in the past decades assessment of discrete hydrogen bonding patterns had received great attention (Steiner, 2002; Desiraju & Steiner, 1999) because of its widespread occurrence in biological systems.

The aim of this paper is to discuss hydrogen patterns assuring the connection between anilinium and hydrogensulfate entities and to establish their different graph-set motifs (Bernstein et al., 1995).

Bis(anilinium hydrogensulfate) is one of the hybrid compounds, rich in H-bonds (Benali-Cherif, Boussekine, et al., 2009; Messai et al., 2009; Benali-Cherif, Falek, et al., 2009), which could have potential importance in constructing sophisticated assemblies from discrete ionic or molecular building blocks due to the strength and the directionality of hydrogen bonds (Steiner et al. 2002, Jayaraman et al., 2002).

Recently, similar structures containing anilinium cations have been reported. Among examples, can be named the folowing ones: anilinium nitrate (Rademeyer, 2004), anilinium picrate (Smith et al., 2004), anilinium hydrogenphosphite and anilinium hydrogenoxalate hemihydrate(Paixão et al., 2000).

The structure of (I) may be described as formed by alternating sheets of cations and anions (Fig. 2) which are held together with four and five-centered N—H···O H-bonds to form C₄⁴(10) infinite chains running through the c direction. Moreover, strong O—H···O hydrogen bonds observed between bisulfate anions generate C₂²(8) chains in the a axis direction. The infinite chains resulting from anion-anion and anion-cation interactions can be described as zigzag layers parallel to the (ac) plane (Fig. 3). The crossing of these chains builds up different rings with R₃³(10) and R₅⁴(16) graph set motifs (Fig. 3) (Etter et al., 1990; Bernstein et al., 1995).

Related literature top

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 top

Single crystals of the title compound are prepared by slow evaporation at room temperature of an aqueous solution of aniline and sulfuric acid.

Computing details top

Data collection: KappaCCD Server Software (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); 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).

Figures top

	Fig. 1. ORTEP view of the asymmetric unit of (I) showing 10% probability displacement ellipsoids.
	Fig. 2. Alternating cationic and anionc layers visualized through the (001) plane.
	Fig. 3. Intermolecular hydrogen bonding patterns running parallel to (bc) plane. H atoms not involved in hydrogen bondings have been omitted for clarity. [Symmetry codes: (i) x-1/2, -y+1, z; (ii) -x+1, -y+1, z+1/2; (iii) -x+1/2, y, z+1/2.

Anilinium hydrogen sulfate top

Crystal data top

C₆H₈N⁺·HSO₄⁻	F(000) = 800
M_r = 191.20	D_x = 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

Data collection top

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

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)] = 0.041	H-atom parameters not refined
wR(F²) = 0.117	w = 1/[σ²(F_o²) + (0.0622P)² + 0.1354P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
4641 reflections	Δρ_max = 0.35 e Å⁻³
219 parameters	Δρ_min = −0.47 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 2096 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.08 (9)

Crystal data top

C₆H₈N⁺·HSO₄⁻	V = 1676.04 (7) Å³
M_r = 191.20	Z = 8
Orthorhombic, Pca2₁	Mo Kα radiation
a = 14.3201 (2) Å	µ = 0.36 mm⁻¹
b = 9.0891 (3) Å	T = 293 K
c = 12.8771 (2) Å	0.2 × 0.15 × 0.1 mm

Data collection top

Nonius KappaCCD diffractometer	3108 reflections with I > 2σ(I)
16963 measured reflections	R_int = 0.049
4641 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	H-atom parameters not refined
wR(F²) = 0.117	Δρ_max = 0.35 e Å⁻³
S = 1.02	Δρ_min = −0.47 e Å⁻³
4641 reflections	Absolute structure: Flack (1983), 2096 Friedel pairs
219 parameters	Absolute structure parameter: 0.08 (9)
1 restraint

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

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

Experimental details

Crystal data
Chemical formula	C₆H₈N⁺·HSO₄⁻
M_r	191.20
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	293
a, b, c (Å)	14.3201 (2), 9.0891 (3), 12.8771 (2)
V (Å³)	1676.04 (7)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.36
Crystal size (mm)	0.2 × 0.15 × 0.1

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	16963, 4641, 3108
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.117, 1.02
No. of reflections	4641
No. of parameters	219
No. of restraints	1
H-atom treatment	H-atom parameters not refined
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.47
Absolute structure	Flack (1983), 2096 Friedel pairs
Absolute structure parameter	0.08 (9)

Computer programs: KappaCCD Server Software (Nonius, 1998), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996), ORTEP-32 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX publication routines (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H11···O1Aⁱ	0.890	1.946	2.821 (2)	167.38
N1B—H2···O3Aⁱⁱ	0.890	2.046	2.867 (3)	152.79
N1A—H33···O2Bⁱⁱⁱ	0.890	2.006	2.884 (3)	168.60
N1B—H3···O1A	0.890	2.583	3.069 (3)	115.14
N1B—H3···O2A	0.890	2.029	2.916 (3)	174.49
N1A—H22···O3B	0.890	1.953	2.817 (4)	163.16
O4A—H4···O3B	0.820	1.786	2.603 (4)	174.56
O4B—H44···O3Aⁱ	0.820	1.841	2.635 (4)	162.51
N1B—H1···O1Bⁱⁱ	0.890	1.941	2.828 (3)	174.68

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

Acknowledgements

We wish to thank Dr M. Giorgi, Faculté des Sciences et Techniques de Saint Jérome, Marseille, France, for providing diffraction facilities and the Centre Universitaire de Khenchela for financial support.

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