8-Hy-droxy-5,7-dimethyl-quinolin-1-ium hydrogen sulfate.

The quinoline ring system of the title salt, C11H12NO(+)·HSO4(-), is essentially planar, with a maximum deviation of 0.054 (2) Å for all non H atoms. In the crystal, the cations and anions are linked via N-H⋯O, O-H⋯O and weak C-H⋯O hydrogen bonds, and are stacked respectively in columns along the a axis. π-π stacking inter-actions, with centroid-centroid distances of 3.5473 (12) and 3.6926 (12) Å, are also observed. The crystal studied was an inversion twin with refined components of 0.43 (7):0.57 (7).

Related literature

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

Experimental

Crystal data

C11H12NO+·HSO4 −

M = 271.28

Orthorhombic,

a = 6.6750 (9) Å

b = 11.6952 (14) Å

c = 14.7283 (18) Å

V = 1149.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.30 mm−1

T = 100 K

0.41 × 0.17 × 0.15 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.889, T max = 0.956

9735 measured reflections

3341 independent reflections

3142 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.103

S = 1.05

3341 reflections

178 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.84 e Å−3

Δρmin = −0.42 e Å−3

Absolute structure: Flack (1983 ▶), 1410 Friedel pairs

Flack parameter: 0.43 (7)

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

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812049483/is5225sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812049483/is5225Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812049483/is5225Isup3.cml

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

C11H12NO+·HSO4−	F(000) = 568
Mr = 271.28	Dx = 1.567 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6153 reflections
a = 6.6750 (9) Å	θ = 2.8–29.9°
b = 11.6952 (14) Å	µ = 0.30 mm−1
c = 14.7283 (18) Å	T = 100 K
V = 1149.8 (3) Å3	Block, yellow
Z = 4	0.41 × 0.17 × 0.15 mm

Bruker APEXII DUO CCD area-detector diffractometer	3341 independent reflections
Radiation source: fine-focus sealed tube	3142 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
φ and ω scans	θmax = 30.0°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→9
Tmin = 0.889, Tmax = 0.956	k = −16→16
9735 measured reflections	l = −20→20

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)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.103	w = 1/[σ2(Fo2) + (0.0699P)2 + 0.0691P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
3341 reflections	Δρmax = 0.84 e Å−3
178 parameters	Δρmin = −0.42 e Å−3
0 restraints	Absolute structure: Flack (1983), 1410 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.43 (7)

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	0.15917 (7)	0.73295 (3)	0.89075 (3)	0.01680 (11)
O1	0.3784 (2)	0.68512 (11)	0.89220 (9)	0.0235 (3)
O2	0.0640 (3)	0.66640 (10)	0.82023 (10)	0.0284 (3)
O3	0.1707 (3)	0.85435 (10)	0.87008 (9)	0.0270 (3)
O4	0.0779 (3)	0.70976 (12)	0.98112 (10)	0.0307 (3)
O5	0.7154 (2)	0.37726 (9)	1.19245 (7)	0.0180 (3)
N1	0.7224 (2)	0.45539 (10)	1.01976 (9)	0.0145 (3)
C1	0.7217 (3)	0.33937 (12)	1.03458 (9)	0.0126 (3)
C2	0.7309 (3)	0.50147 (13)	0.93688 (10)	0.0165 (3)
H2A	0.7349	0.5822	0.9302	0.020*
C3	0.7339 (3)	0.43178 (14)	0.85994 (10)	0.0175 (3)
H3A	0.7394	0.4646	0.8010	0.021*
C4	0.7288 (3)	0.31450 (14)	0.87066 (9)	0.0158 (3)
H4A	0.7283	0.2665	0.8186	0.019*
C5	0.7243 (3)	0.26499 (13)	0.95828 (9)	0.0128 (3)
C6	0.7217 (3)	0.14410 (12)	0.97396 (10)	0.0138 (3)
C7	0.7275 (3)	0.10657 (13)	1.06266 (10)	0.0156 (3)
H7A	0.7291	0.0265	1.0733	0.019*
C8	0.7312 (3)	0.18055 (14)	1.13898 (10)	0.0151 (3)
C9	0.7197 (3)	0.29722 (12)	1.12470 (9)	0.0137 (3)
C10	0.7169 (3)	0.06073 (13)	0.89626 (11)	0.0189 (3)
H10A	0.7094	−0.0174	0.9201	0.028*
H10B	0.8388	0.0692	0.8598	0.028*
H10C	0.5994	0.0760	0.8583	0.028*
C11	0.7464 (3)	0.13120 (14)	1.23285 (11)	0.0203 (4)
H11A	0.8315	0.1804	1.2704	0.030*
H11B	0.8052	0.0545	1.2296	0.030*
H11C	0.6125	0.1264	1.2598	0.030*
H1N1	0.713 (4)	0.5064 (18)	1.0663 (15)	0.015 (5)*
H1O5	0.630 (5)	0.359 (2)	1.227 (2)	0.038 (8)*
H1O1	0.454 (6)	0.718 (3)	0.942 (2)	0.060 (10)*

	U11	U22	U33	U12	U13	U23
S1	0.0199 (2)	0.01535 (16)	0.01516 (16)	0.00047 (15)	−0.00309 (16)	−0.00102 (12)
O1	0.0210 (7)	0.0244 (5)	0.0250 (6)	0.0039 (5)	0.0003 (6)	−0.0053 (5)
O2	0.0380 (9)	0.0183 (5)	0.0289 (6)	−0.0014 (6)	−0.0167 (7)	−0.0033 (5)
O3	0.0395 (9)	0.0146 (5)	0.0268 (6)	−0.0008 (6)	−0.0120 (6)	−0.0010 (4)
O4	0.0316 (8)	0.0373 (7)	0.0232 (6)	0.0046 (7)	0.0116 (6)	0.0026 (5)
O5	0.0252 (7)	0.0174 (5)	0.0113 (4)	−0.0031 (5)	0.0034 (5)	−0.0027 (4)
N1	0.0161 (7)	0.0135 (5)	0.0139 (5)	0.0003 (5)	0.0017 (5)	0.0007 (4)
C1	0.0130 (7)	0.0129 (6)	0.0120 (6)	0.0003 (6)	0.0007 (6)	0.0000 (5)
C2	0.0174 (8)	0.0151 (6)	0.0170 (6)	0.0011 (6)	0.0006 (7)	0.0044 (5)
C3	0.0179 (9)	0.0205 (7)	0.0142 (6)	−0.0002 (7)	0.0005 (7)	0.0039 (5)
C4	0.0169 (8)	0.0193 (6)	0.0112 (6)	−0.0002 (6)	0.0003 (6)	0.0004 (5)
C5	0.0125 (7)	0.0153 (6)	0.0107 (5)	0.0004 (6)	0.0000 (5)	−0.0002 (5)
C6	0.0136 (7)	0.0133 (6)	0.0146 (6)	0.0003 (6)	0.0005 (6)	−0.0020 (5)
C7	0.0151 (8)	0.0141 (6)	0.0177 (6)	0.0007 (6)	0.0018 (6)	0.0012 (5)
C8	0.0139 (8)	0.0180 (6)	0.0134 (6)	0.0006 (6)	0.0011 (6)	0.0016 (5)
C9	0.0159 (7)	0.0156 (6)	0.0098 (6)	−0.0014 (6)	−0.0005 (6)	−0.0008 (5)
C10	0.0219 (9)	0.0172 (6)	0.0176 (6)	−0.0010 (6)	0.0010 (7)	−0.0053 (5)
C11	0.0240 (10)	0.0219 (7)	0.0149 (6)	0.0038 (7)	0.0012 (7)	0.0067 (5)

S1—O2	1.4451 (13)	C4—C5	1.4148 (18)
S1—O3	1.4542 (12)	C4—H4A	0.9500
S1—O4	1.4626 (14)	C5—C6	1.433 (2)
S1—O1	1.5668 (15)	C6—C7	1.379 (2)
O1—H1O1	0.97 (4)	C6—C10	1.504 (2)
O5—C9	1.3685 (17)	C7—C8	1.419 (2)
O5—H1O5	0.79 (3)	C7—H7A	0.9500
N1—C2	1.3355 (18)	C8—C9	1.383 (2)
N1—C1	1.3743 (17)	C8—C11	1.502 (2)
N1—H1N1	0.91 (2)	C10—H10A	0.9800
C1—C9	1.4160 (18)	C10—H10B	0.9800
C1—C5	1.4212 (19)	C10—H10C	0.9800
C2—C3	1.396 (2)	C11—H11A	0.9800
C2—H2A	0.9500	C11—H11B	0.9800
C3—C4	1.381 (2)	C11—H11C	0.9800
C3—H3A	0.9500
O2—S1—O3	113.50 (8)	C1—C5—C6	118.45 (12)
O2—S1—O4	113.03 (10)	C7—C6—C5	117.81 (13)
O3—S1—O4	113.04 (8)	C7—C6—C10	121.01 (13)
O2—S1—O1	103.19 (8)	C5—C6—C10	121.17 (13)
O3—S1—O1	107.56 (9)	C6—C7—C8	123.86 (14)
O4—S1—O1	105.54 (9)	C6—C7—H7A	118.1
S1—O1—H1O1	111 (2)	C8—C7—H7A	118.1
C9—O5—H1O5	108 (2)	C9—C8—C7	118.70 (13)
C2—N1—C1	122.94 (13)	C9—C8—C11	121.54 (14)
C2—N1—H1N1	115.2 (14)	C7—C8—C11	119.75 (14)
C1—N1—H1N1	121.8 (14)	O5—C9—C8	124.42 (13)
N1—C1—C9	119.52 (13)	O5—C9—C1	116.46 (13)
N1—C1—C5	118.60 (13)	C8—C9—C1	119.05 (13)
C9—C1—C5	121.89 (13)	C6—C10—H10A	109.5
N1—C2—C3	120.46 (14)	C6—C10—H10B	109.5
N1—C2—H2A	119.8	H10A—C10—H10B	109.5
C3—C2—H2A	119.8	C6—C10—H10C	109.5
C4—C3—C2	119.12 (14)	H10A—C10—H10C	109.5
C4—C3—H3A	120.4	H10B—C10—H10C	109.5
C2—C3—H3A	120.4	C8—C11—H11A	109.5
C3—C4—C5	120.74 (13)	C8—C11—H11B	109.5
C3—C4—H4A	119.6	H11A—C11—H11B	109.5
C5—C4—H4A	119.6	C8—C11—H11C	109.5
C4—C5—C1	118.11 (13)	H11A—C11—H11C	109.5
C4—C5—C6	123.44 (13)	H11B—C11—H11C	109.5
C2—N1—C1—C9	177.73 (17)	C1—C5—C6—C10	177.83 (16)
C2—N1—C1—C5	−1.9 (3)	C5—C6—C7—C8	1.5 (3)
C1—N1—C2—C3	1.8 (3)	C10—C6—C7—C8	−179.68 (18)
N1—C2—C3—C4	−0.3 (3)	C6—C7—C8—C9	2.9 (3)
C2—C3—C4—C5	−1.2 (3)	C6—C7—C8—C11	−177.37 (18)
C3—C4—C5—C1	1.1 (3)	C7—C8—C9—O5	177.81 (17)
C3—C4—C5—C6	−179.12 (17)	C11—C8—C9—O5	−1.9 (3)
N1—C1—C5—C4	0.4 (2)	C7—C8—C9—C1	−5.3 (3)
C9—C1—C5—C4	−179.20 (17)	C11—C8—C9—C1	175.01 (17)
N1—C1—C5—C6	−179.41 (16)	N1—C1—C9—O5	1.0 (3)
C9—C1—C5—C6	1.0 (3)	C5—C1—C9—O5	−179.39 (16)
C4—C5—C6—C7	176.82 (17)	N1—C1—C9—C8	−176.17 (17)
C1—C5—C6—C7	−3.4 (3)	C5—C1—C9—C8	3.4 (3)
C4—C5—C6—C10	−2.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O3i	0.91 (2)	1.90 (2)	2.7753 (17)	161 (2)
O5—H1O5···O2ii	0.79 (3)	1.91 (3)	2.698 (2)	172 (2)
O1—H1O1···O4i	0.97 (4)	1.64 (4)	2.601 (2)	172 (3)
C3—H3A···O5iii	0.95	2.46	3.3448 (19)	154
C11—H11C···O3ii	0.98	2.50	3.445 (3)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O3i	0.91 (2)	1.90 (2)	2.7753 (17)	161 (2)
O5—H1O5⋯O2ii	0.79 (3)	1.91 (3)	2.698 (2)	172 (2)
O1—H1O1⋯O4i	0.97 (4)	1.64 (4)	2.601 (2)	172 (3)
C3—H3A⋯O5iii	0.95	2.46	3.3448 (19)	154
C11—H11C⋯O3ii	0.98	2.50	3.445 (3)	161

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