Isonicotinium hydrogen sulfate.

The crystal structure of the title compound, C(6)H(6)NO(2) (+)·HSO(4) (-), is stabilized by inter-molecular N-H⋯O and O-H⋯O hydrogen bonds.

Related literature

For background to simple mol­ecular–ionic crystals containing organic cations and acidic anions (1:1 molar ratio), see: Czupiński et al. (2002 ▶); Katrusiak & Szafrański (1999 ▶, 2006 ▶). For a related structure, see: Jebas et al. (2006 ▶).

Experimental

Crystal data

C6H6NO2 +·HSO4 −

M = 221.18

Monoclinic,

a = 8.3816 (17) Å

b = 11.439 (2) Å

c = 9.4057 (19) Å

β = 109.12 (3)°

V = 852.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.39 mm−1

T = 293 K

0.25 × 0.22 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.90, T max = 0.92

8697 measured reflections

1947 independent reflections

1745 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.091

S = 1.14

1947 reflections

128 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.38 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809034916/pv2195sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809034916/pv2195Isup2.hkl

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

C6H6NO2+·HSO4−	F(000) = 456
Mr = 221.18	Dx = 1.716 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1745 reflections
a = 8.3816 (17) Å	θ = 3.1–27.5°
b = 11.439 (2) Å	µ = 0.39 mm−1
c = 9.4057 (19) Å	T = 293 K
β = 109.12 (3)°	Block, colorless
V = 852.0 (3) Å3	0.25 × 0.22 × 0.2 mm
Z = 4

Rigaku SCXmini diffractometer	1947 independent reflections
Radiation source: fine-focus sealed tube	1745 reflections with I > 2σ(I)
graphite	Rint = 0.043
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.1°
ω scans	h = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −14→14
Tmin = 0.90, Tmax = 0.92	l = −12→12
8697 measured reflections

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)] = 0.036	H-atom parameters constrained
wR(F2) = 0.091	w = 1/[σ2(Fo2) + (0.0324P)2 + 0.395P] where P = (Fo2 + 2Fc2)/3
S = 1.14	(Δ/σ)max < 0.001
1947 reflections	Δρmax = 0.29 e Å−3
128 parameters	Δρmin = −0.38 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.164 (6)

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
S1	0.73722 (6)	0.21100 (4)	0.56236 (4)	0.02476 (17)
O2	0.86500 (19)	0.91218 (12)	0.57234 (16)	0.0404 (4)
H2B	0.8723	0.9863	0.5727	0.061*
O6	0.88648 (17)	0.14017 (12)	0.62022 (16)	0.0392 (4)
O1	0.71828 (19)	0.93897 (12)	0.32951 (16)	0.0405 (4)
O5	0.72948 (19)	0.26942 (12)	0.42296 (14)	0.0372 (4)
O4	0.58610 (18)	0.15100 (13)	0.55516 (17)	0.0427 (4)
O3	0.7598 (2)	0.31698 (11)	0.67114 (15)	0.0413 (4)
H3	0.7346	0.3019	0.7594	0.062*
C6	0.7789 (2)	0.87673 (16)	0.4359 (2)	0.0293 (4)
C3	0.7616 (2)	0.74617 (16)	0.42727 (19)	0.0270 (4)
C4	0.8443 (3)	0.67611 (17)	0.5487 (2)	0.0354 (4)
H4A	0.9152	0.7089	0.6374	0.042*
C2	0.6584 (2)	0.69616 (17)	0.2959 (2)	0.0346 (4)
H2A	0.6026	0.7427	0.2135	0.041*
N1	0.7200 (2)	0.51277 (15)	0.4078 (2)	0.0423 (4)
H1A	0.7067	0.4382	0.4019	0.051*
C5	0.8204 (3)	0.55833 (18)	0.5365 (2)	0.0418 (5)
H5A	0.8739	0.5099	0.6175	0.050*
C1	0.6393 (3)	0.57727 (19)	0.2881 (2)	0.0409 (5)
H1B	0.5707	0.5420	0.2002	0.049*

	U11	U22	U33	U12	U13	U23
S1	0.0360 (3)	0.0205 (2)	0.0191 (2)	−0.00064 (16)	0.01072 (17)	−0.00045 (14)
O2	0.0547 (9)	0.0241 (7)	0.0376 (8)	−0.0021 (6)	0.0087 (6)	−0.0019 (6)
O6	0.0381 (8)	0.0309 (7)	0.0407 (8)	0.0034 (6)	0.0023 (6)	−0.0038 (6)
O1	0.0506 (9)	0.0312 (7)	0.0398 (8)	0.0061 (6)	0.0148 (7)	0.0096 (6)
O5	0.0644 (10)	0.0292 (7)	0.0217 (7)	−0.0011 (6)	0.0194 (6)	−0.0001 (5)
O4	0.0385 (8)	0.0453 (9)	0.0477 (9)	−0.0067 (6)	0.0185 (6)	0.0008 (7)
O3	0.0794 (11)	0.0246 (7)	0.0280 (7)	−0.0030 (7)	0.0285 (7)	−0.0051 (5)
C6	0.0293 (9)	0.0258 (9)	0.0345 (10)	0.0018 (7)	0.0128 (7)	0.0022 (7)
C3	0.0284 (9)	0.0258 (9)	0.0294 (9)	0.0011 (7)	0.0130 (7)	0.0014 (7)
C4	0.0413 (11)	0.0296 (9)	0.0332 (10)	0.0013 (8)	0.0094 (8)	0.0017 (8)
C2	0.0341 (10)	0.0337 (10)	0.0343 (10)	0.0003 (8)	0.0090 (8)	0.0002 (8)
N1	0.0540 (11)	0.0234 (8)	0.0569 (12)	−0.0060 (7)	0.0282 (9)	−0.0041 (7)
C5	0.0550 (13)	0.0302 (10)	0.0412 (12)	0.0032 (9)	0.0171 (10)	0.0065 (9)
C1	0.0397 (11)	0.0389 (11)	0.0437 (12)	−0.0079 (9)	0.0133 (9)	−0.0110 (9)

S1—O4	1.4226 (15)	C3—C4	1.382 (3)
S1—O6	1.4393 (14)	C4—C5	1.361 (3)
S1—O5	1.4540 (13)	C4—H4A	0.9300
S1—O3	1.5574 (13)	C2—C1	1.369 (3)
O2—C6	1.314 (2)	C2—H2A	0.9300
O2—H2B	0.8500	N1—C1	1.331 (3)
O1—C6	1.197 (2)	N1—C5	1.334 (3)
O3—H3	0.9372	N1—H1A	0.8600
C6—C3	1.500 (3)	C5—H5A	0.9300
C3—C2	1.379 (3)	C1—H1B	0.9300
O4—S1—O6	113.36 (9)	C5—C4—H4A	120.5
O4—S1—O5	113.76 (9)	C3—C4—H4A	120.5
O6—S1—O5	112.10 (9)	C1—C2—C3	119.23 (19)
O4—S1—O3	108.75 (9)	C1—C2—H2A	120.4
O6—S1—O3	106.64 (9)	C3—C2—H2A	120.4
O5—S1—O3	101.22 (8)	C1—N1—C5	123.11 (18)
C6—O2—H2B	109.1	C1—N1—H1A	118.4
S1—O3—H3	115.1	C5—N1—H1A	118.4
O1—C6—O2	125.44 (18)	N1—C5—C4	119.67 (19)
O1—C6—C3	122.68 (17)	N1—C5—H5A	120.2
O2—C6—C3	111.87 (15)	C4—C5—H5A	120.2
C2—C3—C4	119.86 (18)	N1—C1—C2	119.18 (19)
C2—C3—C6	118.85 (16)	N1—C1—H1B	120.4
C4—C3—C6	121.28 (16)	C2—C1—H1B	120.4
C5—C4—C3	118.95 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2B···O6i	0.85	1.81	2.6425 (19)	166
O3—H3···O5ii	0.94	1.75	2.6543 (18)	160
N1—H1A···O5	0.86	1.94	2.787 (2)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2B⋯O6i	0.85	1.81	2.6425 (19)	166
O3—H3⋯O5ii	0.94	1.75	2.6543 (18)	160
N1—H1A⋯O5	0.86	1.94	2.787 (2)	167

Symmetry codes: (i) ; (ii) .