3-Acetyl-6-chloro-2-methyl-4-phenyl-quinolinium hydrogen sulfate.

In the title salt, C(18)H(15)ClNO(+)·HSO(4) (-), the quinolinium ring system is approximately planar, with a maximum deviation of 0.028 (2) Å, and forms a dihedral angle of 78.43 (4)° with the attached phenyl ring. A pair of inter-molecular O-H⋯O hydrogen bonds links two hydrogen sulfate anions into a dimer, generating a R(2) (2)(8) ring motif. Inter-molecular N-H⋯O hydrogen bonds and C-H⋯O contacts link the ions into a three-dimensional network. The structure is further stabilized by C-H⋯π inter-actions.

Related literature

For the background to and biological activities of quinolines, see: Morimoto et al. (1991 ▶); Michael (1997 ▶); Markees et al. (1970 ▶); Campbell et al. (1988 ▶); Maguire et al. (1994 ▶); Kalluraya & Sreenivasa (1998 ▶); Roma et al. (2000 ▶); Chen et al. (2001 ▶). For related structure: see: Fun et al. (2009 ▶). For hydrogen bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C18H15ClNO+·HSO4 −

M = 393.83

Triclinic,

a = 7.3912 (1) Å

b = 8.8547 (1) Å

c = 13.3413 (2) Å

α = 92.485 (1)°

β = 91.889 (1)°

γ = 99.539 (1)°

V = 859.55 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.37 mm−1

T = 100 K

0.28 × 0.18 × 0.11 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.902, T max = 0.960

20789 measured reflections

5036 independent reflections

4099 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.100

S = 1.05

5036 reflections

299 parameters

All H-atom parameters refined

Δρmax = 0.49 e Å−3

Δρmin = −0.46 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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/S1600536809048934/tk2576sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809048934/tk2576Isup2.hkl

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

C18H15ClNO+·HSO4−	Z = 2
Mr = 393.83	F(000) = 408
Triclinic, P1	Dx = 1.522 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3912 (1) Å	Cell parameters from 6943 reflections
b = 8.8547 (1) Å	θ = 2.3–30.0°
c = 13.3413 (2) Å	µ = 0.37 mm−1
α = 92.485 (1)°	T = 100 K
β = 91.889 (1)°	Block, colourless
γ = 99.539 (1)°	0.28 × 0.18 × 0.11 mm
V = 859.55 (2) Å3

Bruker SMART APEXII CCD area-detector diffractometer	5036 independent reflections
Radiation source: fine-focus sealed tube	4099 reflections with I > 2σ(I)
graphite	Rint = 0.036
φ and ω scans	θmax = 30.1°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −10→10
Tmin = 0.902, Tmax = 0.960	k = −12→12
20789 measured reflections	l = −17→18

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	All H-atom parameters refined
S = 1.05	w = 1/[σ2(Fo2) + (0.0423P)2 + 0.5203P] where P = (Fo2 + 2Fc2)/3
5036 reflections	(Δ/σ)max < 0.001
299 parameters	Δρmax = 0.49 e Å−3
0 restraints	Δρmin = −0.46 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems 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
Cl1	−0.07965 (6)	1.15710 (5)	0.87223 (3)	0.02195 (11)
O1	0.84858 (17)	0.74796 (14)	0.81500 (10)	0.0227 (3)
N1	0.56245 (19)	1.06536 (16)	0.64462 (11)	0.0144 (3)
C1	0.3576 (2)	0.98834 (18)	0.77580 (12)	0.0130 (3)
C2	0.2022 (2)	1.01001 (19)	0.83015 (13)	0.0153 (3)
C3	0.1135 (2)	1.12951 (19)	0.80771 (13)	0.0161 (3)
C4	0.1734 (2)	1.23192 (19)	0.73288 (13)	0.0174 (3)
C5	0.3223 (2)	1.21203 (19)	0.67852 (13)	0.0163 (3)
C6	0.4145 (2)	1.08892 (18)	0.69952 (12)	0.0138 (3)
C7	0.6577 (2)	0.95245 (18)	0.65899 (12)	0.0144 (3)
C8	0.6082 (2)	0.85283 (17)	0.73720 (12)	0.0135 (3)
C9	0.4607 (2)	0.86836 (17)	0.79479 (12)	0.0128 (3)
C10	0.4060 (2)	0.76276 (17)	0.87655 (12)	0.0131 (3)
C11	0.5030 (2)	0.78222 (19)	0.96875 (13)	0.0165 (3)
C12	0.4476 (2)	0.6859 (2)	1.04564 (13)	0.0178 (3)
C13	0.2988 (2)	0.56871 (19)	1.02989 (14)	0.0184 (3)
C14	0.2033 (2)	0.54837 (19)	0.93779 (14)	0.0185 (3)
C15	0.2549 (2)	0.64550 (19)	0.86090 (13)	0.0163 (3)
C16	0.8098 (2)	0.9359 (2)	0.59146 (14)	0.0191 (3)
C17	0.7189 (2)	0.72549 (19)	0.75589 (13)	0.0157 (3)
C18	0.6537 (3)	0.5756 (2)	0.69949 (16)	0.0243 (4)
S1	0.21895 (5)	0.66550 (5)	0.53846 (3)	0.01523 (10)
O3	0.22537 (17)	0.50022 (14)	0.54897 (10)	0.0226 (3)
O2	0.09255 (19)	0.67613 (15)	0.44494 (10)	0.0218 (3)
O4	0.14599 (19)	0.73228 (17)	0.62452 (10)	0.0284 (3)
O5	0.39820 (17)	0.74590 (14)	0.51153 (10)	0.0217 (3)
H2A	0.158 (3)	0.941 (2)	0.8811 (15)	0.014 (5)*
H4A	0.108 (3)	1.313 (2)	0.7209 (16)	0.024 (5)*
H5A	0.363 (3)	1.281 (2)	0.6270 (16)	0.023 (5)*
H11A	0.606 (3)	0.861 (2)	0.9797 (16)	0.023 (5)*
H12A	0.513 (3)	0.700 (2)	1.1086 (16)	0.019 (5)*
H13A	0.258 (3)	0.501 (2)	1.0818 (17)	0.026 (6)*
H14A	0.100 (3)	0.468 (2)	0.9267 (16)	0.025 (5)*
H15A	0.189 (3)	0.634 (2)	0.7994 (15)	0.016 (5)*
H18A	0.736 (3)	0.507 (3)	0.7149 (18)	0.038 (7)*
H18B	0.536 (3)	0.538 (3)	0.7207 (18)	0.032 (6)*
H18C	0.641 (3)	0.587 (3)	0.631 (2)	0.039 (7)*
H16A	0.772 (4)	0.847 (3)	0.548 (2)	0.057 (8)*
H16B	0.838 (4)	1.017 (3)	0.552 (2)	0.042 (7)*
H16C	0.921 (4)	0.922 (3)	0.6250 (19)	0.039 (7)*
H1N1	0.592 (3)	1.124 (3)	0.5945 (18)	0.032 (6)*
H1O2	−0.001 (5)	0.624 (4)	0.447 (2)	0.070 (11)*

	U11	U22	U33	U12	U13	U23
Cl1	0.01539 (19)	0.0206 (2)	0.0306 (2)	0.00572 (15)	0.00463 (16)	−0.00319 (17)
O1	0.0157 (6)	0.0233 (6)	0.0296 (7)	0.0043 (5)	−0.0031 (5)	0.0052 (5)
N1	0.0154 (6)	0.0136 (6)	0.0140 (7)	0.0013 (5)	0.0007 (5)	0.0032 (5)
C1	0.0121 (7)	0.0123 (7)	0.0143 (7)	0.0013 (5)	−0.0003 (6)	−0.0004 (6)
C2	0.0130 (7)	0.0154 (7)	0.0168 (8)	0.0004 (6)	0.0000 (6)	−0.0004 (6)
C3	0.0126 (7)	0.0169 (7)	0.0186 (8)	0.0031 (6)	−0.0001 (6)	−0.0042 (6)
C4	0.0193 (8)	0.0147 (7)	0.0188 (8)	0.0057 (6)	−0.0043 (6)	−0.0009 (6)
C5	0.0185 (8)	0.0147 (7)	0.0155 (8)	0.0027 (6)	−0.0027 (6)	0.0003 (6)
C6	0.0140 (7)	0.0133 (7)	0.0136 (8)	0.0011 (6)	−0.0002 (6)	−0.0004 (6)
C7	0.0129 (7)	0.0148 (7)	0.0147 (8)	0.0004 (6)	−0.0006 (6)	0.0001 (6)
C8	0.0130 (7)	0.0124 (7)	0.0149 (8)	0.0015 (6)	−0.0005 (6)	0.0007 (6)
C9	0.0123 (7)	0.0123 (7)	0.0129 (7)	−0.0002 (6)	−0.0015 (6)	−0.0011 (6)
C10	0.0124 (7)	0.0128 (7)	0.0151 (8)	0.0042 (6)	0.0036 (6)	0.0017 (6)
C11	0.0152 (8)	0.0163 (7)	0.0175 (8)	0.0017 (6)	−0.0002 (6)	0.0006 (6)
C12	0.0189 (8)	0.0219 (8)	0.0142 (8)	0.0079 (6)	0.0006 (6)	0.0023 (6)
C13	0.0211 (8)	0.0168 (8)	0.0198 (9)	0.0078 (6)	0.0080 (7)	0.0056 (6)
C14	0.0171 (8)	0.0157 (8)	0.0221 (9)	0.0006 (6)	0.0055 (7)	0.0013 (6)
C15	0.0144 (7)	0.0180 (8)	0.0163 (8)	0.0017 (6)	0.0002 (6)	0.0014 (6)
C16	0.0170 (8)	0.0205 (8)	0.0202 (9)	0.0028 (7)	0.0050 (7)	0.0049 (7)
C17	0.0141 (7)	0.0175 (8)	0.0168 (8)	0.0043 (6)	0.0046 (6)	0.0052 (6)
C18	0.0292 (10)	0.0202 (9)	0.0253 (10)	0.0104 (8)	−0.0030 (8)	−0.0014 (7)
S1	0.01399 (19)	0.01650 (19)	0.0145 (2)	0.00016 (14)	−0.00041 (14)	0.00325 (14)
O3	0.0195 (6)	0.0172 (6)	0.0317 (7)	0.0035 (5)	−0.0023 (5)	0.0090 (5)
O2	0.0197 (6)	0.0224 (6)	0.0219 (7)	−0.0004 (5)	−0.0081 (5)	0.0066 (5)
O4	0.0267 (7)	0.0362 (8)	0.0224 (7)	0.0081 (6)	0.0001 (6)	−0.0061 (6)
O5	0.0152 (6)	0.0243 (6)	0.0239 (7)	−0.0029 (5)	−0.0023 (5)	0.0094 (5)

Cl1—C3	1.7373 (17)	C11—C12	1.391 (2)
O1—C17	1.206 (2)	C11—H11A	0.95 (2)
N1—C7	1.332 (2)	C12—C13	1.385 (3)
N1—C6	1.375 (2)	C12—H12A	0.95 (2)
N1—H1N1	0.88 (2)	C13—C14	1.386 (3)
C1—C6	1.410 (2)	C13—H13A	0.96 (2)
C1—C2	1.414 (2)	C14—C15	1.390 (2)
C1—C9	1.433 (2)	C14—H14A	0.95 (2)
C2—C3	1.372 (2)	C15—H15A	0.93 (2)
C2—H2A	0.961 (19)	C16—H16A	0.96 (3)
C3—C4	1.410 (2)	C16—H16B	0.91 (3)
C4—C5	1.369 (2)	C16—H16C	0.95 (3)
C4—H4A	0.95 (2)	C17—C18	1.496 (3)
C5—C6	1.411 (2)	C18—H18A	0.95 (3)
C5—H5A	0.96 (2)	C18—H18B	0.94 (3)
C7—C8	1.414 (2)	C18—H18C	0.92 (3)
C7—C16	1.486 (2)	S1—O4	1.4306 (14)
C8—C9	1.376 (2)	S1—O5	1.4602 (13)
C8—C17	1.523 (2)	S1—O3	1.4846 (12)
C9—C10	1.490 (2)	S1—O2	1.5495 (13)
C10—C11	1.393 (2)	O2—H1O2	0.77 (3)
C10—C15	1.396 (2)
C7—N1—C6	124.00 (14)	C10—C11—H11A	120.5 (13)
C7—N1—H1N1	117.5 (16)	C13—C12—C11	120.13 (16)
C6—N1—H1N1	118.4 (16)	C13—C12—H12A	120.1 (12)
C6—C1—C2	118.86 (14)	C11—C12—H12A	119.7 (13)
C6—C1—C9	118.26 (14)	C12—C13—C14	120.02 (16)
C2—C1—C9	122.87 (15)	C12—C13—H13A	121.6 (13)
C3—C2—C1	118.80 (15)	C14—C13—H13A	118.4 (14)
C3—C2—H2A	120.3 (12)	C13—C14—C15	120.51 (16)
C1—C2—H2A	120.9 (12)	C13—C14—H14A	120.4 (13)
C2—C3—C4	122.16 (16)	C15—C14—H14A	119.1 (13)
C2—C3—Cl1	119.71 (13)	C14—C15—C10	119.42 (16)
C4—C3—Cl1	118.13 (13)	C14—C15—H15A	121.0 (12)
C5—C4—C3	120.02 (15)	C10—C15—H15A	119.6 (12)
C5—C4—H4A	121.3 (13)	C7—C16—H16A	108.2 (18)
C3—C4—H4A	118.7 (13)	C7—C16—H16B	113.0 (17)
C4—C5—C6	118.85 (15)	H16A—C16—H16B	107 (2)
C4—C5—H5A	120.4 (13)	C7—C16—H16C	114.5 (15)
C6—C5—H5A	120.8 (13)	H16A—C16—H16C	107 (2)
N1—C6—C1	118.95 (14)	H16B—C16—H16C	107 (2)
N1—C6—C5	119.76 (14)	O1—C17—C18	123.85 (16)
C1—C6—C5	121.29 (15)	O1—C17—C8	119.92 (15)
N1—C7—C8	118.46 (15)	C18—C17—C8	116.21 (15)
N1—C7—C16	118.53 (15)	C17—C18—H18A	108.6 (15)
C8—C7—C16	123.01 (14)	C17—C18—H18B	107.4 (15)
C9—C8—C7	120.87 (14)	H18A—C18—H18B	111 (2)
C9—C8—C17	120.18 (14)	C17—C18—H18C	112.1 (15)
C7—C8—C17	118.94 (14)	H18A—C18—H18C	112 (2)
C8—C9—C1	119.40 (14)	H18B—C18—H18C	106 (2)
C8—C9—C10	121.29 (14)	O4—S1—O5	114.16 (8)
C1—C9—C10	119.31 (14)	O4—S1—O3	112.00 (8)
C11—C10—C15	120.07 (15)	O5—S1—O3	110.14 (8)
C11—C10—C9	120.25 (14)	O4—S1—O2	109.30 (8)
C15—C10—C9	119.68 (14)	O5—S1—O2	104.05 (8)
C12—C11—C10	119.83 (16)	O3—S1—O2	106.62 (7)
C12—C11—H11A	119.6 (13)	S1—O2—H1O2	112 (2)
C6—C1—C2—C3	−0.9 (2)	C7—C8—C9—C10	179.22 (15)
C9—C1—C2—C3	179.05 (15)	C17—C8—C9—C10	0.3 (2)
C1—C2—C3—C4	−0.5 (3)	C6—C1—C9—C8	−1.4 (2)
C1—C2—C3—Cl1	179.14 (12)	C2—C1—C9—C8	178.66 (15)
C2—C3—C4—C5	1.3 (3)	C6—C1—C9—C10	178.62 (14)
Cl1—C3—C4—C5	−178.37 (13)	C2—C1—C9—C10	−1.3 (2)
C3—C4—C5—C6	−0.6 (2)	C8—C9—C10—C11	78.3 (2)
C7—N1—C6—C1	−0.2 (2)	C1—C9—C10—C11	−101.73 (18)
C7—N1—C6—C5	−179.97 (15)	C8—C9—C10—C15	−102.73 (19)
C2—C1—C6—N1	−178.14 (14)	C1—C9—C10—C15	77.3 (2)
C9—C1—C6—N1	1.9 (2)	C15—C10—C11—C12	−0.9 (2)
C2—C1—C6—C5	1.6 (2)	C9—C10—C11—C12	178.09 (15)
C9—C1—C6—C5	−178.35 (15)	C10—C11—C12—C13	1.5 (3)
C4—C5—C6—N1	178.89 (15)	C11—C12—C13—C14	−0.8 (3)
C4—C5—C6—C1	−0.8 (2)	C12—C13—C14—C15	−0.4 (3)
C6—N1—C7—C8	−1.9 (2)	C13—C14—C15—C10	1.0 (3)
C6—N1—C7—C16	177.43 (15)	C11—C10—C15—C14	−0.3 (2)
N1—C7—C8—C9	2.4 (2)	C9—C10—C15—C14	−179.33 (15)
C16—C7—C8—C9	−176.91 (16)	C9—C8—C17—O1	−89.5 (2)
N1—C7—C8—C17	−178.63 (14)	C7—C8—C17—O1	91.6 (2)
C16—C7—C8—C17	2.0 (2)	C9—C8—C17—C18	89.0 (2)
C7—C8—C9—C1	−0.8 (2)	C7—C8—C17—C18	−89.93 (19)
C17—C8—C9—C1	−179.69 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O5i	0.88 (2)	1.86 (2)	2.7200 (19)	168 (2)
O2—H1O2···O3ii	0.77 (4)	1.84 (4)	2.6027 (19)	180 (5)
C5—H5A···O3iii	0.96 (2)	2.58 (2)	3.304 (2)	132.5 (17)
C15—H15A···O4	0.93 (2)	2.55 (2)	3.381 (2)	148.0 (15)
C16—H16C···O4iv	0.95 (3)	2.55 (3)	3.332 (2)	139 (2)
C12—H12A···Cg1v	0.95 (2)	2.74 (2)	3.5884 (18)	149.1 (14)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O5i	0.88 (2)	1.86 (2)	2.7200 (19)	168 (2)
O2—H1O2⋯O3ii	0.77 (4)	1.84 (4)	2.6027 (19)	180 (5)
C5—H5A⋯O3iii	0.96 (2)	2.58 (2)	3.304 (2)	132.5 (17)
C15—H15A⋯O4	0.93 (2)	2.55 (2)	3.381 (2)	148.0 (15)
C16—H16C⋯O4iv	0.95 (3)	2.55 (3)	3.332 (2)	139 (2)
C12—H12A⋯Cg1v	0.95 (2)	2.74 (2)	3.5884 (18)	149.1 (14)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) . Cg1 is the centroid of the C1–C6 ring.