Nicotinium hydrogen sulfate.

The structure of title compound, C(6)H(6)NO(2) (+)·HSO(4) (-), comprises discrete ions which are inter-conected by N-H⋯O and O-H⋯O hydrogen bonds, leading to a neutral one-dimensional network along [001]. These hydrogen bonds appear to complement the Coulombic inter-action and help to stabilize the structure further.

Related literature

For simple mol­ecular–ionic crystals containing organic cations and acid radicals (1:1 molar ratio), see: Czupiński et al. (2002 ▶); Katrusiak & Szafrański (1999 ▶, 2006 ▶). For the structure of dinicotinium sulfate, see: Athimoolam & Rajaram (2005 ▶).

Experimental

Crystal data

C6H6NO2 +·HSO4 −

M = 221.19

Monoclinic,

a = 8.2654 (17) Å

b = 11.545 (2) Å

c = 9.4669 (19) Å

β = 109.43 (3)°

V = 851.9 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.39 mm−1

T = 293 K

0.25 × 0.2 × 0.2 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.91, T max = 0.93

8643 measured reflections

1949 independent reflections

1788 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.090

S = 1.14

1949 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.49 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/S1600536809034928/bx2233sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809034928/bx2233Isup2.hkl

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

C6H6NO2+·HSO4−	F(000) = 456
Mr = 221.19	Dx = 1.725 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1788 reflections
a = 8.2654 (17) Å	θ = 3.2–27.5°
b = 11.545 (2) Å	µ = 0.39 mm−1
c = 9.4669 (19) Å	T = 293 K
β = 109.43 (3)°	Block, colorless
V = 851.9 (3) Å3	0.25 × 0.2 × 0.2 mm
Z = 4

Rigaku SCXmini diffractometer	1949 independent reflections
Radiation source: fine-focus sealed tube	1788 reflections with I > 2σ(I)
graphite	Rint = 0.029
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.2°
ω scans	h = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −14→14
Tmin = 0.91, Tmax = 0.93	l = −12→12
8643 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H-atom parameters constrained
S = 1.14	w = 1/[σ2(Fo2) + (0.0405P)2 + 0.3479P] where P = (Fo2 + 2Fc2)/3
1949 reflections	(Δ/σ)max = 0.001
127 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.49 e Å−3

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	0.75328 (5)	0.70391 (3)	0.56623 (4)	0.02440 (13)
O1	0.71400 (17)	0.45258 (11)	0.34210 (15)	0.0396 (3)
O2	0.87198 (17)	0.40764 (11)	0.57869 (13)	0.0382 (3)
H2B	0.8839	0.4807	0.5877	0.057*
O3	0.90270 (15)	0.63375 (11)	0.64101 (13)	0.0340 (3)
O4	0.59511 (16)	0.64255 (12)	0.54911 (14)	0.0391 (3)
O5	0.75643 (18)	0.75578 (12)	0.42787 (13)	0.0395 (3)
O6	0.76089 (19)	0.81232 (11)	0.66597 (13)	0.0414 (4)
H1	0.7597	0.7975	0.7581	0.062*
N1	0.60598 (19)	0.10546 (14)	0.25572 (17)	0.0366 (4)
H1B	0.5361	0.0840	0.1701	0.044*
C4	0.75053 (19)	0.25493 (14)	0.41590 (17)	0.0259 (3)
C5	0.6393 (2)	0.21802 (15)	0.27984 (19)	0.0312 (4)
H5A	0.5877	0.2715	0.2050	0.037*
C3	0.8265 (2)	0.17308 (15)	0.52470 (19)	0.0334 (4)
H3A	0.9031	0.1960	0.6169	0.040*
C2	0.7879 (3)	0.05679 (16)	0.4957 (2)	0.0422 (4)
H2A	0.8372	0.0013	0.5685	0.051*
C6	0.7770 (2)	0.38299 (15)	0.43965 (18)	0.0282 (3)
C1	0.6761 (3)	0.02450 (16)	0.3583 (2)	0.0414 (4)
H1A	0.6494	−0.0532	0.3370	0.050*

	U11	U22	U33	U12	U13	U23
S1	0.0327 (2)	0.0247 (2)	0.01610 (19)	0.00166 (15)	0.00847 (15)	−0.00001 (13)
O1	0.0447 (7)	0.0301 (7)	0.0398 (7)	0.0039 (6)	0.0083 (6)	0.0078 (5)
O2	0.0476 (7)	0.0270 (6)	0.0332 (7)	−0.0027 (5)	0.0044 (5)	−0.0032 (5)
O3	0.0314 (6)	0.0327 (6)	0.0306 (6)	0.0016 (5)	0.0007 (5)	−0.0031 (5)
O4	0.0306 (6)	0.0493 (8)	0.0370 (7)	−0.0028 (6)	0.0104 (5)	0.0001 (6)
O5	0.0642 (9)	0.0384 (7)	0.0199 (6)	0.0022 (6)	0.0195 (6)	0.0021 (5)
O6	0.0776 (10)	0.0271 (6)	0.0241 (6)	0.0051 (6)	0.0230 (6)	−0.0019 (5)
N1	0.0338 (8)	0.0376 (8)	0.0334 (8)	−0.0030 (6)	0.0045 (6)	−0.0106 (6)
C4	0.0231 (7)	0.0274 (8)	0.0265 (8)	0.0008 (6)	0.0073 (6)	−0.0005 (6)
C5	0.0295 (8)	0.0336 (9)	0.0274 (8)	0.0029 (7)	0.0051 (6)	0.0002 (7)
C3	0.0338 (9)	0.0312 (9)	0.0291 (8)	0.0010 (7)	0.0025 (7)	0.0018 (7)
C2	0.0512 (11)	0.0281 (9)	0.0417 (11)	0.0031 (8)	0.0079 (8)	0.0069 (8)
C6	0.0251 (7)	0.0280 (8)	0.0309 (8)	0.0007 (6)	0.0086 (6)	0.0016 (6)
C1	0.0461 (11)	0.0268 (9)	0.0501 (11)	−0.0043 (8)	0.0145 (9)	−0.0059 (8)

S1—O4	1.4478 (13)	N1—H1B	0.8600
S1—O5	1.4483 (12)	C4—C5	1.377 (2)
S1—O3	1.4493 (13)	C4—C3	1.385 (2)
S1—O6	1.5565 (12)	C4—C6	1.500 (2)
O1—C6	1.204 (2)	C5—H5A	0.9300
O2—C6	1.320 (2)	C3—C2	1.386 (3)
O2—H2B	0.8501	C3—H3A	0.9300
O6—H1	0.8921	C2—C1	1.373 (3)
N1—C5	1.332 (2)	C2—H2A	0.9300
N1—C1	1.334 (2)	C1—H1A	0.9300
O4—S1—O5	112.85 (8)	N1—C5—H5A	120.1
O4—S1—O3	111.86 (8)	C4—C5—H5A	120.1
O5—S1—O3	113.83 (8)	C4—C3—C2	119.75 (16)
O4—S1—O6	108.30 (8)	C4—C3—H3A	120.1
O5—S1—O6	101.94 (7)	C2—C3—H3A	120.1
O3—S1—O6	107.28 (8)	C1—C2—C3	119.25 (17)
C6—O2—H2B	108.9	C1—C2—H2A	120.4
S1—O6—H1	115.3	C3—C2—H2A	120.4
C5—N1—C1	122.94 (16)	O1—C6—O2	125.66 (16)
C5—N1—H1B	118.5	O1—C6—C4	122.57 (15)
C1—N1—H1B	118.5	O2—C6—C4	111.75 (14)
C5—C4—C3	118.73 (16)	N1—C1—C2	119.48 (17)
C5—C4—C6	117.62 (15)	N1—C1—H1A	120.3
C3—C4—C6	123.61 (15)	C2—C1—H1A	120.3
N1—C5—C4	119.85 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2B···O3	0.85	1.83	2.6697 (18)	169
O6—H1···O5i	0.89	1.73	2.6129 (17)	170
N1—H1B···O4ii	0.86	2.11	2.843 (2)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2B⋯O3	0.85	1.83	2.6697 (18)	169
O6—H1⋯O5i	0.89	1.73	2.6129 (17)	170
N1—H1B⋯O4ii	0.86	2.11	2.843 (2)	143

Symmetry codes: (i) ; (ii) .