2-Cyano-quinolin-1-ium hydrogen sulfate.

The title salt, C(10)H(7)N(2) (+)·HSO(4) (-), is formed by the transfer of a proton from H(2)SO(4) to the N atom of 2-cyano-quinoline during crystallization. The quinoline ring system is approximately planar with a maximum deviation of 0.013 (3) Å. In the crystal, the cations are linked to the anions via inter-molecular N-H⋯O, O-H⋯O and C-H⋯O hydrogen bonds, forming a layered network.

Related literature

For background to and the biological activity of quinoline derivatives, see: Loh et al. (2010a ▶ ▶,b); Sasaki et al. (1998 ▶); Reux et al. (2009 ▶); Morimoto et al. (1991 ▶); Michael (1997 ▶); Markees et al. (1970 ▶); Campbell et al. (1988 ▶). For related structures, see: Loh et al. (2010a ▶,b ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C10H7N2 +·HSO4 −

M = 252.24

Triclinic,

a = 7.2154 (3) Å

b = 8.2334 (4) Å

c = 9.9985 (4) Å

α = 110.622 (2)°

β = 90.982 (3)°

γ = 110.791 (2)°

V = 512.82 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.32 mm−1

T = 100 K

0.34 × 0.19 × 0.12 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.900, T max = 0.963

5740 measured reflections

1979 independent reflections

1721 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.154

S = 1.11

1979 reflections

186 parameters

All H-atom parameters refined

Δρmax = 0.82 e Å−3

Δρmin = −0.56 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681003878X/hb5657sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681003878X/hb5657Isup2.hkl

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

C10H7N2+·HSO4−	Z = 2
Mr = 252.24	F(000) = 260
Triclinic, P1	Dx = 1.634 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2154 (3) Å	Cell parameters from 2998 reflections
b = 8.2334 (4) Å	θ = 2.2–27.6°
c = 9.9985 (4) Å	µ = 0.32 mm−1
α = 110.622 (2)°	T = 100 K
β = 90.982 (3)°	Block, colourless
γ = 110.791 (2)°	0.34 × 0.19 × 0.12 mm
V = 512.82 (4) Å3

Bruker SMART APEXII CCD diffractometer	1979 independent reflections
Radiation source: fine-focus sealed tube	1721 reflections with I > 2σ(I)
graphite	Rint = 0.032
φ and ω scans	θmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→6
Tmin = 0.900, Tmax = 0.963	k = −10→10
5740 measured reflections	l = −12→12

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154	All H-atom parameters refined
S = 1.11	w = 1/[σ2(Fo2) + (0.0884P)2 + 0.5522P] where P = (Fo2 + 2Fc2)/3
1979 reflections	(Δ/σ)max < 0.001
186 parameters	Δρmax = 0.82 e Å−3
0 restraints	Δρmin = −0.56 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.15454 (10)	0.99553 (10)	0.33365 (7)	0.0141 (3)
O1	0.3450 (3)	1.0495 (3)	0.4227 (2)	0.0216 (5)
O2	0.0561 (3)	1.1258 (3)	0.3966 (2)	0.0184 (5)
O3	0.1678 (3)	0.9584 (3)	0.1832 (2)	0.0199 (5)
O4	0.0149 (3)	0.8001 (3)	0.3345 (3)	0.0213 (5)
N1	0.5709 (4)	0.3044 (3)	0.6749 (3)	0.0153 (5)
N2	0.7421 (5)	0.4421 (4)	0.4025 (3)	0.0341 (8)
C1	0.5498 (4)	0.2853 (4)	0.8046 (3)	0.0146 (6)
C2	0.3903 (4)	0.1311 (4)	0.8119 (3)	0.0171 (6)
C3	0.3736 (5)	0.1152 (4)	0.9439 (3)	0.0176 (6)
C4	0.5161 (4)	0.2496 (4)	1.0697 (3)	0.0178 (7)
C5	0.6693 (4)	0.3999 (4)	1.0632 (3)	0.0157 (6)
C6	0.6915 (4)	0.4236 (4)	0.9298 (3)	0.0151 (6)
C7	0.8438 (4)	0.5775 (4)	0.9151 (3)	0.0161 (6)
C8	0.8587 (4)	0.5909 (4)	0.7818 (3)	0.0164 (6)
C9	0.7188 (4)	0.4485 (4)	0.6622 (3)	0.0171 (6)
C10	0.7297 (5)	0.4459 (4)	0.5172 (3)	0.0224 (7)
H2A	0.305 (5)	0.040 (5)	0.730 (4)	0.017 (8)*
H3A	0.266 (5)	0.008 (5)	0.947 (4)	0.018 (8)*
H4A	0.493 (5)	0.226 (5)	1.157 (4)	0.025 (9)*
H5A	0.767 (4)	0.498 (4)	1.148 (3)	0.008 (7)*
H7A	0.933 (5)	0.672 (5)	0.999 (4)	0.016 (8)*
H8A	0.964 (5)	0.696 (5)	0.767 (4)	0.015 (8)*
H1N1	0.474 (6)	0.211 (6)	0.589 (5)	0.045 (11)*
H1O4	−0.005 (7)	0.814 (7)	0.402 (5)	0.040 (14)*

	U11	U22	U33	U12	U13	U23
S1	0.0155 (4)	0.0150 (4)	0.0056 (4)	0.0016 (3)	−0.0029 (3)	0.0015 (3)
O1	0.0213 (11)	0.0246 (12)	0.0092 (10)	0.0065 (9)	−0.0058 (8)	−0.0016 (9)
O2	0.0221 (11)	0.0209 (11)	0.0133 (10)	0.0093 (9)	0.0018 (8)	0.0069 (9)
O3	0.0229 (11)	0.0231 (12)	0.0058 (10)	0.0025 (9)	0.0009 (8)	0.0031 (9)
O4	0.0286 (13)	0.0204 (12)	0.0079 (11)	0.0045 (10)	0.0005 (9)	0.0028 (10)
N1	0.0176 (13)	0.0158 (13)	0.0088 (12)	0.0046 (10)	−0.0020 (10)	0.0025 (10)
N2	0.0415 (18)	0.0289 (16)	0.0134 (14)	−0.0059 (14)	−0.0036 (12)	0.0070 (12)
C1	0.0183 (15)	0.0194 (15)	0.0080 (13)	0.0100 (12)	0.0014 (11)	0.0047 (12)
C2	0.0155 (14)	0.0167 (15)	0.0130 (15)	0.0041 (12)	−0.0030 (12)	0.0013 (12)
C3	0.0175 (15)	0.0185 (16)	0.0148 (15)	0.0047 (13)	−0.0003 (12)	0.0066 (13)
C4	0.0218 (16)	0.0229 (16)	0.0113 (15)	0.0116 (13)	0.0031 (12)	0.0063 (13)
C5	0.0183 (15)	0.0199 (15)	0.0079 (14)	0.0094 (13)	−0.0005 (11)	0.0023 (12)
C6	0.0159 (14)	0.0145 (15)	0.0122 (14)	0.0051 (12)	−0.0019 (11)	0.0030 (12)
C7	0.0197 (15)	0.0157 (15)	0.0093 (14)	0.0073 (12)	−0.0016 (12)	0.0004 (12)
C8	0.0154 (14)	0.0162 (15)	0.0134 (14)	0.0033 (12)	−0.0013 (11)	0.0039 (12)
C9	0.0209 (15)	0.0182 (15)	0.0113 (14)	0.0069 (12)	0.0007 (11)	0.0055 (12)
C10	0.0259 (17)	0.0183 (16)	0.0134 (16)	0.0001 (13)	−0.0026 (12)	0.0040 (13)

S1—O3	1.438 (2)	C3—C4	1.425 (4)
S1—O1	1.457 (2)	C3—H3A	0.96 (3)
S1—O2	1.460 (2)	C4—C5	1.358 (4)
S1—O4	1.570 (2)	C4—H4A	0.96 (4)
O4—H1O4	0.67 (5)	C5—C6	1.418 (4)
N1—C9	1.333 (4)	C5—H5A	0.98 (3)
N1—C1	1.365 (4)	C6—C7	1.408 (4)
N1—H1N1	0.98 (5)	C7—C8	1.378 (4)
N2—C10	1.142 (4)	C7—H7A	0.95 (4)
C1—C2	1.404 (4)	C8—C9	1.398 (4)
C1—C6	1.426 (4)	C8—H8A	0.99 (3)
C2—C3	1.375 (4)	C9—C10	1.446 (4)
C2—H2A	0.91 (3)
O3—S1—O1	113.75 (13)	C5—C4—C3	120.9 (3)
O3—S1—O2	113.56 (12)	C5—C4—H4A	124 (2)
O1—S1—O2	111.77 (12)	C3—C4—H4A	115 (2)
O3—S1—O4	104.10 (13)	C4—C5—C6	120.2 (3)
O1—S1—O4	105.98 (13)	C4—C5—H5A	123.1 (17)
O2—S1—O4	106.81 (13)	C6—C5—H5A	116.7 (17)
S1—O4—H1O4	108 (4)	C7—C6—C5	123.5 (3)
C9—N1—C1	122.0 (2)	C7—C6—C1	118.5 (3)
C9—N1—H1N1	119 (3)	C5—C6—C1	118.0 (3)
C1—N1—H1N1	119 (3)	C8—C7—C6	120.6 (3)
N1—C1—C2	119.6 (3)	C8—C7—H7A	121 (2)
N1—C1—C6	118.8 (3)	C6—C7—H7A	118 (2)
C2—C1—C6	121.7 (3)	C7—C8—C9	118.4 (3)
C3—C2—C1	118.2 (3)	C7—C8—H8A	122.8 (19)
C3—C2—H2A	121 (2)	C9—C8—H8A	118.8 (19)
C1—C2—H2A	121 (2)	N1—C9—C8	121.7 (3)
C2—C3—C4	121.0 (3)	N1—C9—C10	116.2 (3)
C2—C3—H3A	117 (2)	C8—C9—C10	122.1 (3)
C4—C3—H3A	121 (2)	N2—C10—C9	178.2 (4)
C9—N1—C1—C2	179.6 (3)	C2—C1—C6—C7	−178.0 (3)
C9—N1—C1—C6	−0.5 (4)	N1—C1—C6—C5	−179.0 (2)
N1—C1—C2—C3	179.7 (3)	C2—C1—C6—C5	1.0 (4)
C6—C1—C2—C3	−0.3 (4)	C5—C6—C7—C8	179.2 (3)
C1—C2—C3—C4	−1.1 (5)	C1—C6—C7—C8	−1.9 (4)
C2—C3—C4—C5	1.8 (5)	C6—C7—C8—C9	0.2 (4)
C3—C4—C5—C6	−1.1 (4)	C1—N1—C9—C8	−1.4 (4)
C4—C5—C6—C7	178.7 (3)	C1—N1—C9—C10	176.8 (3)
C4—C5—C6—C1	−0.3 (4)	C7—C8—C9—N1	1.5 (5)
N1—C1—C6—C7	2.0 (4)	C7—C8—C9—C10	−176.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1i	0.98 (5)	1.71 (5)	2.669 (3)	169 (4)
O4—H1O4···O2ii	0.67 (5)	1.97 (5)	2.641 (3)	176 (7)
C2—H2A···O2iii	0.91 (4)	2.53 (4)	3.320 (4)	145 (3)
C5—H5A···O4iv	0.98 (3)	2.52 (3)	3.475 (4)	166 (3)
C7—H7A···O3iv	0.94 (4)	2.41 (4)	3.338 (4)	167 (3)
C8—H8A···O2v	0.99 (4)	2.59 (4)	3.309 (4)	130 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1i	0.98 (5)	1.71 (5)	2.669 (3)	169 (4)
O4—H1O4⋯O2ii	0.67 (5)	1.97 (5)	2.641 (3)	176 (7)
C2—H2A⋯O2iii	0.91 (4)	2.53 (4)	3.320 (4)	145 (3)
C5—H5A⋯O4iv	0.98 (3)	2.52 (3)	3.475 (4)	166 (3)
C7—H7A⋯O3iv	0.94 (4)	2.41 (4)	3.338 (4)	167 (3)
C8—H8A⋯O2v	0.99 (4)	2.59 (4)	3.309 (4)	130 (3)

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