3-Acetyl-6-chloro-2-methyl-4-phenyl-quinolinium perchlorate.

In the title mol-ecular salt, C(18)H(15)ClNO(+)·ClO(4) (-), the quinolin-ium ring system is approximately planar, with a maximum deviation of 0.027 (1) Å. The dihedral angle formed between the mean planes of the quinolinium ring system and the benzene ring is 78.46 (3)°. In the crystal structure, inter-molecular N-H⋯O and C-H⋯O hydrogen bonds link the cations and anions into a three-dimensional network. The crystal structure is further consolidated by C-H⋯π inter-actions.

Related literature

For natural products containing quinolines, see: Michael (1997 ▶); Morimoto et al. (1991 ▶). For the biological activities of quinolines, see: Campbell et al. (1988 ▶); Markees et al. (1970 ▶). For the physiological activities of quinolines, see: Katritzky & Arend (1998 ▶); Jiang & Si (2002 ▶). For related structures, see: Shahani et al. (2010 ▶); Fun et al. (2009 ▶); Loh et al. (2010 ▶). 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

C18H15ClNO+·ClO4 −

M = 396.21

Triclinic,

a = 7.3862 (1) Å

b = 8.8519 (2) Å

c = 13.3378 (3) Å

α = 92.477 (1)°

β = 91.903 (1)°

γ = 99.550 (1)°

V = 858.44 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.41 mm−1

T = 100 K

0.58 × 0.54 × 0.27 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.797, T max = 0.898

27967 measured reflections

7482 independent reflections

6933 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.108

S = 1.09

7482 reflections

295 parameters

All H-atom parameters refined

Δρmax = 0.69 e Å−3

Δρmin = −1.00 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/S1600536810012900/hb5397sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810012900/hb5397Isup2.hkl

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

C18H15ClNO+·ClO4−	Z = 2
Mr = 396.21	F(000) = 408
Triclinic, P1	Dx = 1.533 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3862 (1) Å	Cell parameters from 9929 reflections
b = 8.8519 (2) Å	θ = 2.7–35.1°
c = 13.3378 (3) Å	µ = 0.41 mm−1
α = 92.477 (1)°	T = 100 K
β = 91.903 (1)°	Block, colourless
γ = 99.550 (1)°	0.58 × 0.54 × 0.27 mm
V = 858.44 (3) Å3

Bruker SMART APEXII CCD diffractometer	7482 independent reflections
Radiation source: fine-focus sealed tube	6933 reflections with I > 2σ(I)
graphite	Rint = 0.019
φ and ω scans	θmax = 35.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
Tmin = 0.797, Tmax = 0.898	k = −13→14
27967 measured reflections	l = −21→21

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	All H-atom parameters refined
S = 1.09	w = 1/[σ2(Fo2) + (0.0636P)2 + 0.2949P] where P = (Fo2 + 2Fc2)/3
7482 reflections	(Δ/σ)max < 0.001
295 parameters	Δρmax = 0.69 e Å−3
0 restraints	Δρmin = −1.00 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 esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.57962 (3)	−0.15711 (3)	0.127788 (19)	0.01984 (6)
O1	−0.34868 (10)	0.25202 (9)	0.18488 (6)	0.02125 (14)
N1	−0.06256 (10)	−0.06546 (8)	0.35547 (5)	0.01256 (12)
C1	−0.15762 (11)	0.04733 (9)	0.34086 (6)	0.01226 (13)
C2	0.08539 (11)	−0.08886 (9)	0.30060 (6)	0.01178 (13)
C3	0.17738 (12)	−0.21217 (10)	0.32169 (6)	0.01442 (14)
C4	0.32724 (13)	−0.23218 (10)	0.26722 (7)	0.01553 (14)
C5	0.38693 (12)	−0.12954 (10)	0.19231 (7)	0.01427 (14)
C6	0.29771 (11)	−0.01015 (9)	0.16974 (6)	0.01300 (13)
C7	0.14195 (11)	0.01160 (9)	0.22419 (6)	0.01113 (12)
C8	0.03934 (11)	0.13153 (9)	0.20510 (6)	0.01083 (12)
C9	−0.10849 (11)	0.14720 (9)	0.26283 (6)	0.01146 (12)
C10	0.09383 (11)	0.23714 (9)	0.12361 (6)	0.01128 (12)
C11	−0.00355 (12)	0.21724 (10)	0.03113 (6)	0.01471 (14)
C12	0.05201 (13)	0.31380 (11)	−0.04601 (7)	0.01646 (15)
C13	0.20163 (13)	0.43138 (10)	−0.03026 (7)	0.01619 (15)
C14	0.29697 (13)	0.45204 (10)	0.06228 (7)	0.01649 (15)
C15	0.24533 (12)	0.35437 (10)	0.13932 (6)	0.01454 (14)
C16	−0.21861 (12)	0.27461 (10)	0.24424 (6)	0.01340 (13)
C17	−0.15358 (17)	0.42459 (12)	0.30030 (8)	0.02276 (18)
C18	−0.31035 (13)	0.06418 (11)	0.40871 (7)	0.01699 (15)
H3A	0.137 (2)	−0.2799 (18)	0.3733 (12)	0.017 (3)*
H4A	0.394 (3)	−0.310 (2)	0.2795 (13)	0.029 (4)*
H6A	0.343 (2)	0.0569 (18)	0.1200 (11)	0.016 (3)*
H11A	−0.117 (2)	0.1334 (19)	0.0189 (12)	0.022 (4)*
H12A	−0.013 (2)	0.2955 (19)	−0.1119 (13)	0.023 (4)*
H13A	0.239 (2)	0.5034 (19)	−0.0772 (12)	0.021 (4)*
H14A	0.394 (2)	0.5305 (19)	0.0737 (12)	0.021 (4)*
H15A	0.306 (2)	0.3656 (18)	0.2039 (12)	0.020 (4)*
H17A	−0.033 (3)	0.460 (2)	0.2780 (14)	0.031 (4)*
H17B	−0.242 (3)	0.488 (2)	0.2843 (15)	0.037 (5)*
H17C	−0.153 (3)	0.418 (3)	0.3570 (18)	0.045 (6)*
H18A	−0.281 (3)	0.154 (3)	0.4486 (16)	0.042 (5)*
H18B	−0.424 (3)	0.078 (2)	0.3754 (14)	0.031 (4)*
H18C	−0.334 (3)	−0.026 (2)	0.4431 (15)	0.037 (5)*
H1N1	−0.089 (3)	−0.121 (2)	0.4034 (14)	0.030 (4)*
Cl2	0.28102 (3)	0.33444 (2)	0.461521 (15)	0.01541 (5)
O2	0.27428 (10)	0.49972 (8)	0.45103 (6)	0.02070 (14)
O3	0.10191 (10)	0.25407 (9)	0.48844 (6)	0.01977 (14)
O4	0.40805 (10)	0.32400 (9)	0.55505 (5)	0.01960 (13)
O5	0.35420 (12)	0.26779 (11)	0.37509 (6)	0.02648 (16)

	U11	U22	U33	U12	U13	U23
Cl1	0.01521 (10)	0.01761 (10)	0.02749 (11)	0.00551 (7)	0.00402 (7)	−0.00306 (8)
O1	0.0153 (3)	0.0210 (3)	0.0279 (4)	0.0044 (2)	−0.0042 (2)	0.0044 (3)
N1	0.0142 (3)	0.0112 (3)	0.0124 (3)	0.0017 (2)	0.0016 (2)	0.0031 (2)
C1	0.0126 (3)	0.0116 (3)	0.0126 (3)	0.0015 (2)	0.0012 (2)	0.0020 (2)
C2	0.0132 (3)	0.0103 (3)	0.0118 (3)	0.0020 (2)	−0.0002 (2)	0.0013 (2)
C3	0.0180 (3)	0.0117 (3)	0.0140 (3)	0.0042 (3)	−0.0018 (3)	0.0020 (2)
C4	0.0176 (4)	0.0132 (3)	0.0166 (3)	0.0058 (3)	−0.0025 (3)	0.0003 (3)
C5	0.0129 (3)	0.0133 (3)	0.0170 (3)	0.0039 (2)	−0.0002 (3)	−0.0016 (3)
C6	0.0128 (3)	0.0118 (3)	0.0146 (3)	0.0025 (2)	0.0011 (2)	0.0005 (2)
C7	0.0116 (3)	0.0100 (3)	0.0119 (3)	0.0021 (2)	0.0001 (2)	0.0011 (2)
C8	0.0113 (3)	0.0095 (3)	0.0116 (3)	0.0012 (2)	0.0002 (2)	0.0018 (2)
C9	0.0116 (3)	0.0108 (3)	0.0122 (3)	0.0020 (2)	0.0011 (2)	0.0024 (2)
C10	0.0122 (3)	0.0104 (3)	0.0116 (3)	0.0023 (2)	0.0016 (2)	0.0025 (2)
C11	0.0155 (3)	0.0150 (3)	0.0133 (3)	0.0014 (3)	−0.0009 (2)	0.0024 (3)
C12	0.0191 (4)	0.0187 (4)	0.0126 (3)	0.0050 (3)	0.0013 (3)	0.0038 (3)
C13	0.0195 (4)	0.0149 (3)	0.0159 (3)	0.0057 (3)	0.0063 (3)	0.0054 (3)
C14	0.0170 (4)	0.0140 (3)	0.0180 (3)	−0.0002 (3)	0.0045 (3)	0.0033 (3)
C15	0.0143 (3)	0.0141 (3)	0.0144 (3)	−0.0002 (3)	0.0010 (2)	0.0022 (2)
C16	0.0132 (3)	0.0136 (3)	0.0146 (3)	0.0042 (2)	0.0033 (2)	0.0042 (2)
C17	0.0308 (5)	0.0161 (4)	0.0229 (4)	0.0101 (3)	−0.0037 (4)	−0.0030 (3)
C18	0.0164 (4)	0.0185 (4)	0.0171 (3)	0.0039 (3)	0.0060 (3)	0.0045 (3)
Cl2	0.01584 (9)	0.01583 (9)	0.01397 (9)	0.00038 (6)	−0.00013 (6)	0.00351 (6)
O2	0.0187 (3)	0.0142 (3)	0.0297 (4)	0.0028 (2)	−0.0018 (3)	0.0094 (2)
O3	0.0148 (3)	0.0220 (3)	0.0209 (3)	−0.0037 (2)	−0.0018 (2)	0.0106 (2)
O4	0.0200 (3)	0.0196 (3)	0.0181 (3)	0.0001 (2)	−0.0077 (2)	0.0070 (2)
O5	0.0264 (4)	0.0343 (4)	0.0192 (3)	0.0083 (3)	0.0016 (3)	−0.0065 (3)

Cl1—C5	1.7332 (9)	C10—C15	1.3976 (12)
O1—C16	1.2090 (11)	C11—C12	1.3946 (12)
N1—C1	1.3296 (11)	C11—H11A	1.025 (17)
N1—C2	1.3740 (11)	C12—C13	1.3903 (14)
N1—H1N1	0.829 (19)	C12—H12A	0.981 (17)
C1—C9	1.4123 (11)	C13—C14	1.3903 (13)
C1—C18	1.4919 (12)	C13—H13A	0.929 (16)
C2—C7	1.4097 (11)	C14—C15	1.3936 (12)
C2—C3	1.4115 (12)	C14—H14A	0.917 (17)
C3—C4	1.3754 (13)	C15—H15A	0.952 (16)
C3—H3A	0.954 (16)	C16—C17	1.4937 (14)
C4—C5	1.4117 (13)	C17—H17A	0.956 (19)
C4—H4A	0.926 (19)	C17—H17B	0.95 (2)
C5—C6	1.3738 (12)	C17—H17C	0.76 (2)
C6—C7	1.4159 (11)	C18—H18A	0.93 (2)
C6—H6A	0.942 (15)	C18—H18B	0.963 (19)
C7—C8	1.4295 (11)	C18—H18C	0.93 (2)
C8—C9	1.3788 (11)	Cl2—O5	1.4344 (8)
C8—C10	1.4864 (11)	Cl2—O3	1.4583 (7)
C9—C16	1.5200 (12)	Cl2—O2	1.4846 (7)
C10—C11	1.3965 (11)	Cl2—O4	1.5512 (7)
C1—N1—C2	123.82 (7)	C10—C11—H11A	121.2 (9)
C1—N1—H1N1	118.1 (13)	C13—C12—C11	120.12 (8)
C2—N1—H1N1	117.9 (13)	C13—C12—H12A	120.6 (10)
N1—C1—C9	118.77 (7)	C11—C12—H12A	119.3 (10)
N1—C1—C18	118.45 (7)	C12—C13—C14	119.96 (8)
C9—C1—C18	122.77 (8)	C12—C13—H13A	123.8 (10)
N1—C2—C7	118.94 (7)	C14—C13—H13A	116.1 (10)
N1—C2—C3	119.61 (7)	C13—C14—C15	120.52 (8)
C7—C2—C3	121.45 (8)	C13—C14—H14A	120.5 (10)
C4—C3—C2	118.80 (8)	C15—C14—H14A	119.0 (10)
C4—C3—H3A	120.4 (10)	C14—C15—C10	119.40 (8)
C2—C3—H3A	120.8 (10)	C14—C15—H15A	123.0 (10)
C3—C4—C5	119.88 (8)	C10—C15—H15A	117.5 (10)
C3—C4—H4A	121.9 (11)	O1—C16—C17	123.74 (8)
C5—C4—H4A	118.2 (11)	O1—C16—C9	119.76 (8)
C6—C5—C4	122.16 (8)	C17—C16—C9	116.48 (8)
C6—C5—Cl1	119.75 (7)	C16—C17—H17A	106.1 (11)
C4—C5—Cl1	118.09 (7)	C16—C17—H17B	105.6 (12)
C5—C6—C7	118.88 (8)	H17A—C17—H17B	114.6 (16)
C5—C6—H6A	119.5 (10)	C16—C17—H17C	112.6 (17)
C7—C6—H6A	121.6 (10)	H17A—C17—H17C	111 (2)
C2—C7—C6	118.79 (7)	H17B—C17—H17C	107 (2)
C2—C7—C8	118.43 (7)	C1—C18—H18A	110.3 (13)
C6—C7—C8	122.77 (7)	C1—C18—H18B	115.2 (11)
C9—C8—C7	119.31 (7)	H18A—C18—H18B	101.8 (17)
C9—C8—C10	121.17 (7)	C1—C18—H18C	106.8 (13)
C7—C8—C10	119.52 (7)	H18A—C18—H18C	115.6 (17)
C8—C9—C1	120.67 (7)	H18B—C18—H18C	107.4 (16)
C8—C9—C16	120.14 (7)	O5—Cl2—O3	114.23 (5)
C1—C9—C16	119.18 (7)	O5—Cl2—O2	111.92 (5)
C11—C10—C15	120.21 (7)	O3—Cl2—O2	110.06 (5)
C11—C10—C8	120.13 (7)	O5—Cl2—O4	109.31 (5)
C15—C10—C8	119.65 (7)	O3—Cl2—O4	104.17 (4)
C12—C11—C10	119.78 (8)	O2—Cl2—O4	106.60 (4)
C12—C11—H11A	119.0 (9)
C2—N1—C1—C9	1.85 (12)	C7—C8—C9—C16	179.58 (7)
C2—N1—C1—C18	−177.33 (8)	C10—C8—C9—C16	−0.34 (12)
C1—N1—C2—C7	0.14 (12)	N1—C1—C9—C8	−2.26 (12)
C1—N1—C2—C3	−179.90 (8)	C18—C1—C9—C8	176.88 (8)
N1—C2—C3—C4	−178.83 (8)	N1—C1—C9—C16	178.84 (7)
C7—C2—C3—C4	1.12 (13)	C18—C1—C9—C16	−2.01 (12)
C2—C3—C4—C5	0.44 (13)	C9—C8—C10—C11	−78.54 (10)
C3—C4—C5—C6	−1.37 (13)	C7—C8—C10—C11	101.54 (10)
C3—C4—C5—Cl1	178.54 (7)	C9—C8—C10—C15	102.80 (10)
C4—C5—C6—C7	0.70 (13)	C7—C8—C10—C15	−77.12 (10)
Cl1—C5—C6—C7	−179.20 (6)	C15—C10—C11—C12	0.67 (13)
N1—C2—C7—C6	178.19 (7)	C8—C10—C11—C12	−177.97 (8)
C3—C2—C7—C6	−1.77 (12)	C10—C11—C12—C13	−1.27 (14)
N1—C2—C7—C8	−1.72 (11)	C11—C12—C13—C14	0.51 (14)
C3—C2—C7—C8	178.32 (7)	C12—C13—C14—C15	0.86 (14)
C5—C6—C7—C2	0.84 (12)	C13—C14—C15—C10	−1.44 (14)
C5—C6—C7—C8	−179.25 (8)	C11—C10—C15—C14	0.67 (13)
C2—C7—C8—C9	1.28 (11)	C8—C10—C15—C14	179.32 (8)
C6—C7—C8—C9	−178.63 (7)	C8—C9—C16—O1	89.51 (11)
C2—C7—C8—C10	−178.80 (7)	C1—C9—C16—O1	−91.59 (10)
C6—C7—C8—C10	1.30 (12)	C8—C9—C16—C17	−88.92 (10)
C7—C8—C9—C1	0.70 (12)	C1—C9—C16—C17	89.98 (10)
C10—C8—C9—C1	−179.22 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O3i	0.832 (18)	1.896 (18)	2.7177 (10)	169 (2)
C3—H3A···O2ii	0.955 (16)	2.583 (16)	3.3010 (11)	132.2 (12)
C15—H15A···O5	0.951 (16)	2.512 (16)	3.3716 (12)	150.4 (13)
C18—H18B···O5iii	0.97 (2)	2.53 (2)	3.3266 (13)	139.5 (14)
C12—H12A···Cg1iv	0.981 (17)	2.694 (17)	3.5810 (10)	150.6 (13)

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C10–C15 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O3i	0.832 (18)	1.896 (18)	2.7177 (10)	169 (2)
C3—H3A⋯O2ii	0.955 (16)	2.583 (16)	3.3010 (11)	132.2 (12)
C15—H15A⋯O5	0.951 (16)	2.512 (16)	3.3716 (12)	150.4 (13)
C18—H18B⋯O5iii	0.97 (2)	2.53 (2)	3.3266 (13)	139.5 (14)
C12—H12A⋯Cg1iv	0.981 (17)	2.694 (17)	3.5810 (10)	150.6 (13)

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