3-Acetyl-2-methyl-4-phenyl-quinolin-1-ium chloride.

An N-H⋯Cl hydrogen bond connects the ions in the title salt, C(18)H(16)NO(+)·Cl(-). The quinolin-1-ium residue is almost planar (r.m.s. deviation = 0.020 Å) but both the acetyl group [O-C-C-C torsion angle = 62.73 (17)°] and adjacent benzene ring [C-C-C-C torsion angle = -104.06 (14)°] are twisted out of this plane; the acetyl and benzene substituents are non-parallel [dihedral angle = 66.16 (7)°]. The crystal packing is consolidated by C-H⋯O and C-H⋯Cl contacts.

Related literature

For background to the pharmaceutical potential of quinoline derivatives, see: Musiol et al. (2006 ▶). For related structures, see: Kaiser et al. (2009 ▶); Viji et al. (2010 ▶).

Experimental

Crystal data

C18H16NO+·Cl−

M = 297.77

Monoclinic,

a = 9.5046 (8) Å

b = 8.5787 (8) Å

c = 18.2538 (16) Å

β = 94.282 (1)°

V = 1484.2 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 100 K

0.32 × 0.23 × 0.17 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.972, T max = 0.980

13696 measured reflections

3409 independent reflections

3047 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.086

S = 1.07

3409 reflections

195 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810027017/pk2254sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810027017/pk2254Isup2.hkl

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

C18H16NO+·Cl−	F(000) = 624
Mr = 297.77	Dx = 1.333 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6610 reflections
a = 9.5046 (8) Å	θ = 2.6–28.2°
b = 8.5787 (8) Å	µ = 0.26 mm−1
c = 18.2538 (16) Å	T = 100 K
β = 94.282 (1)°	Block, colourless
V = 1484.2 (2) Å3	0.32 × 0.23 × 0.17 mm
Z = 4

Bruker SMART APEX diffractometer	3409 independent reflections
Radiation source: fine-focus sealed tube	3047 reflections with I > 2σ(I)
graphite	Rint = 0.028
ω scans	θmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.972, Tmax = 0.980	k = −10→11
13696 measured reflections	l = −23→23

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) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0335P)2 + 0.8555P] where P = (Fo2 + 2Fc2)/3
3409 reflections	(Δ/σ)max = 0.001
195 parameters	Δρmax = 0.34 e Å−3
1 restraint	Δρmin = −0.18 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	−0.23118 (3)	0.81420 (4)	0.951338 (18)	0.01937 (10)
O1	−0.07410 (11)	0.19289 (12)	0.74963 (6)	0.0263 (2)
N1	−0.02654 (11)	0.56664 (13)	0.90768 (6)	0.0153 (2)
H1N	−0.0898 (14)	0.6344 (16)	0.9209 (8)	0.018*
C1	0.02975 (15)	0.03841 (16)	0.84768 (8)	0.0223 (3)
H1A	−0.0480	0.0080	0.8770	0.033*
H1B	0.1158	0.0528	0.8800	0.033*
H1C	0.0453	−0.0434	0.8117	0.033*
C2	−0.00653 (14)	0.18746 (16)	0.80845 (7)	0.0173 (3)
C3	0.03851 (13)	0.33644 (15)	0.84823 (7)	0.0151 (3)
C4	−0.06597 (13)	0.43859 (15)	0.87103 (7)	0.0158 (3)
C5	0.11193 (13)	0.60797 (15)	0.92460 (7)	0.0144 (3)
C6	0.14307 (14)	0.74822 (16)	0.96245 (7)	0.0173 (3)
H6	0.0695	0.8120	0.9783	0.021*
C7	0.28135 (15)	0.79106 (16)	0.97607 (7)	0.0191 (3)
H7	0.3036	0.8861	1.0010	0.023*
C8	0.39122 (14)	0.69582 (16)	0.95347 (7)	0.0190 (3)
H8	0.4866	0.7273	0.9633	0.023*
C9	0.36130 (13)	0.55823 (16)	0.91736 (7)	0.0168 (3)
H9	0.4361	0.4947	0.9027	0.020*
C10	0.21954 (13)	0.51013 (15)	0.90172 (7)	0.0144 (3)
C11	0.18018 (13)	0.37150 (15)	0.86232 (7)	0.0143 (2)
C12	−0.22057 (14)	0.41010 (17)	0.85588 (8)	0.0210 (3)
H12A	−0.2734	0.4809	0.8858	0.031*
H12B	−0.2423	0.3020	0.8682	0.031*
H12C	−0.2473	0.4288	0.8037	0.031*
C13	0.29118 (13)	0.27584 (15)	0.83041 (7)	0.0151 (3)
C14	0.30263 (14)	0.28491 (15)	0.75478 (7)	0.0174 (3)
H14	0.2337	0.3400	0.7245	0.021*
C15	0.41504 (15)	0.21323 (16)	0.72377 (8)	0.0202 (3)
H15	0.4251	0.2230	0.6726	0.024*
C16	0.51255 (15)	0.12761 (17)	0.76727 (8)	0.0211 (3)
H16	0.5900	0.0800	0.7460	0.025*
C17	0.49715 (14)	0.11120 (17)	0.84204 (8)	0.0209 (3)
H17	0.5613	0.0480	0.8713	0.025*
C18	0.38782 (14)	0.18724 (16)	0.87403 (7)	0.0181 (3)
H18	0.3790	0.1788	0.9254	0.022*

	U11	U22	U33	U12	U13	U23
Cl1	0.01572 (16)	0.02029 (17)	0.02252 (17)	0.00187 (12)	0.00424 (12)	−0.00375 (12)
O1	0.0321 (6)	0.0224 (5)	0.0233 (5)	−0.0033 (4)	−0.0061 (4)	−0.0023 (4)
N1	0.0142 (5)	0.0150 (5)	0.0168 (5)	0.0020 (4)	0.0024 (4)	0.0003 (4)
C1	0.0245 (7)	0.0154 (7)	0.0267 (7)	−0.0032 (5)	−0.0010 (6)	0.0007 (5)
C2	0.0150 (6)	0.0171 (6)	0.0201 (6)	−0.0021 (5)	0.0031 (5)	−0.0017 (5)
C3	0.0168 (6)	0.0137 (6)	0.0148 (6)	−0.0007 (5)	0.0009 (5)	0.0019 (5)
C4	0.0157 (6)	0.0164 (6)	0.0154 (6)	−0.0005 (5)	0.0015 (5)	0.0028 (5)
C5	0.0148 (6)	0.0152 (6)	0.0133 (6)	−0.0003 (5)	0.0013 (4)	0.0021 (5)
C6	0.0203 (6)	0.0151 (6)	0.0168 (6)	0.0026 (5)	0.0019 (5)	−0.0004 (5)
C7	0.0231 (7)	0.0150 (6)	0.0189 (6)	−0.0021 (5)	−0.0006 (5)	−0.0024 (5)
C8	0.0159 (6)	0.0212 (7)	0.0196 (6)	−0.0035 (5)	−0.0001 (5)	−0.0007 (5)
C9	0.0148 (6)	0.0179 (6)	0.0178 (6)	0.0006 (5)	0.0020 (5)	0.0005 (5)
C10	0.0152 (6)	0.0145 (6)	0.0136 (6)	0.0002 (5)	0.0013 (4)	0.0014 (5)
C11	0.0157 (6)	0.0140 (6)	0.0133 (6)	0.0005 (5)	0.0017 (5)	0.0017 (5)
C12	0.0136 (6)	0.0221 (7)	0.0272 (7)	−0.0012 (5)	0.0011 (5)	−0.0018 (6)
C13	0.0140 (6)	0.0133 (6)	0.0181 (6)	−0.0013 (5)	0.0021 (5)	−0.0018 (5)
C14	0.0185 (6)	0.0150 (6)	0.0185 (6)	0.0004 (5)	0.0000 (5)	−0.0002 (5)
C15	0.0237 (7)	0.0197 (7)	0.0175 (6)	−0.0004 (5)	0.0043 (5)	−0.0021 (5)
C16	0.0192 (6)	0.0196 (7)	0.0251 (7)	0.0027 (5)	0.0046 (5)	−0.0053 (6)
C17	0.0185 (6)	0.0199 (7)	0.0238 (7)	0.0044 (5)	−0.0022 (5)	−0.0016 (5)
C18	0.0190 (6)	0.0185 (7)	0.0168 (6)	0.0009 (5)	0.0002 (5)	−0.0005 (5)

O1—C2	1.2100 (17)	C8—H8	0.9500
N1—C4	1.3257 (17)	C9—C10	1.4177 (18)
N1—C5	1.3756 (16)	C9—H9	0.9500
N1—H1N	0.883 (9)	C10—C11	1.4253 (18)
C1—C2	1.4933 (19)	C11—C13	1.4892 (17)
C1—H1A	0.9800	C12—H12A	0.9800
C1—H1B	0.9800	C12—H12B	0.9800
C1—H1C	0.9800	C12—H12C	0.9800
C2—C3	1.5158 (18)	C13—C18	1.3950 (19)
C3—C11	1.3849 (18)	C13—C14	1.3951 (18)
C3—C4	1.4103 (18)	C14—C15	1.3893 (19)
C4—C12	1.4949 (18)	C14—H14	0.9500
C5—C6	1.4079 (18)	C15—C16	1.385 (2)
C5—C10	1.4102 (17)	C15—H15	0.9500
C6—C7	1.3695 (19)	C16—C17	1.391 (2)
C6—H6	0.9500	C16—H16	0.9500
C7—C8	1.4116 (19)	C17—C18	1.3917 (19)
C7—H7	0.9500	C17—H17	0.9500
C8—C9	1.3713 (19)	C18—H18	0.9500
C4—N1—C5	123.81 (11)	C10—C9—H9	119.8
C4—N1—H1N	120.7 (11)	C5—C10—C9	117.81 (12)
C5—N1—H1N	115.4 (11)	C5—C10—C11	118.50 (11)
C2—C1—H1A	109.5	C9—C10—C11	123.66 (12)
C2—C1—H1B	109.5	C3—C11—C10	119.33 (12)
H1A—C1—H1B	109.5	C3—C11—C13	121.00 (12)
C2—C1—H1C	109.5	C10—C11—C13	119.36 (11)
H1A—C1—H1C	109.5	C4—C12—H12A	109.5
H1B—C1—H1C	109.5	C4—C12—H12B	109.5
O1—C2—C1	123.14 (13)	H12A—C12—H12B	109.5
O1—C2—C3	120.32 (12)	C4—C12—H12C	109.5
C1—C2—C3	116.45 (11)	H12A—C12—H12C	109.5
C11—C3—C4	120.43 (12)	H12B—C12—H12C	109.5
C11—C3—C2	120.53 (12)	C18—C13—C14	119.90 (12)
C4—C3—C2	119.04 (11)	C18—C13—C11	122.18 (11)
N1—C4—C3	119.02 (12)	C14—C13—C11	117.79 (12)
N1—C4—C12	117.76 (12)	C15—C14—C13	119.85 (12)
C3—C4—C12	123.22 (12)	C15—C14—H14	120.1
N1—C5—C6	119.53 (11)	C13—C14—H14	120.1
N1—C5—C10	118.88 (12)	C16—C15—C14	120.20 (12)
C6—C5—C10	121.56 (12)	C16—C15—H15	119.9
C7—C6—C5	118.82 (12)	C14—C15—H15	119.9
C7—C6—H6	120.6	C15—C16—C17	120.09 (13)
C5—C6—H6	120.6	C15—C16—H16	120.0
C6—C7—C8	120.84 (13)	C17—C16—H16	120.0
C6—C7—H7	119.6	C16—C17—C18	120.06 (13)
C8—C7—H7	119.6	C16—C17—H17	120.0
C9—C8—C7	120.48 (12)	C18—C17—H17	120.0
C9—C8—H8	119.8	C17—C18—C13	119.76 (12)
C7—C8—H8	119.8	C17—C18—H18	120.1
C8—C9—C10	120.48 (12)	C13—C18—H18	120.1
C8—C9—H9	119.8
O1—C2—C3—C11	−117.58 (15)	C8—C9—C10—C11	177.83 (12)
C1—C2—C3—C11	65.82 (16)	C4—C3—C11—C10	1.52 (18)
O1—C2—C3—C4	62.73 (17)	C2—C3—C11—C10	−178.17 (11)
C1—C2—C3—C4	−113.87 (14)	C4—C3—C11—C13	−172.07 (12)
C5—N1—C4—C3	0.68 (19)	C2—C3—C11—C13	8.24 (18)
C5—N1—C4—C12	−179.25 (12)	C5—C10—C11—C3	−0.50 (18)
C11—C3—C4—N1	−1.62 (19)	C9—C10—C11—C3	−178.43 (12)
C2—C3—C4—N1	178.07 (11)	C5—C10—C11—C13	173.20 (11)
C11—C3—C4—C12	178.31 (12)	C9—C10—C11—C13	−4.74 (19)
C2—C3—C4—C12	−2.00 (19)	C3—C11—C13—C18	−114.69 (15)
C4—N1—C5—C6	178.67 (12)	C10—C11—C13—C18	71.73 (17)
C4—N1—C5—C10	0.33 (18)	C3—C11—C13—C14	69.53 (16)
N1—C5—C6—C7	−177.19 (12)	C10—C11—C13—C14	−104.06 (14)
C10—C5—C6—C7	1.11 (19)	C18—C13—C14—C15	−3.8 (2)
C5—C6—C7—C8	−0.8 (2)	C11—C13—C14—C15	172.11 (12)
C6—C7—C8—C9	0.0 (2)	C13—C14—C15—C16	2.6 (2)
C7—C8—C9—C10	0.5 (2)	C14—C15—C16—C17	0.9 (2)
N1—C5—C10—C9	177.64 (11)	C15—C16—C17—C18	−3.3 (2)
C6—C5—C10—C9	−0.67 (18)	C16—C17—C18—C13	2.1 (2)
N1—C5—C10—C11	−0.42 (17)	C14—C13—C18—C17	1.5 (2)
C6—C5—C10—C11	−178.72 (12)	C11—C13—C18—C17	−174.24 (12)
C8—C9—C10—C5	−0.12 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···Cl1	0.883 (14)	2.146 (14)	3.0265 (12)	175.2 (13)
C1—H1c···O1i	0.98	2.55	3.4972 (18)	163
C1—H1a···Cl1ii	0.98	2.83	3.7592 (15)	159
C7—H7···Cl1iii	0.95	2.82	3.6803 (14)	152
C8—H8···Cl1iv	0.95	2.81	3.7329 (14)	165
C18—H18···Cl1v	0.95	2.74	3.6175 (14)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯Cl1	0.88 (1)	2.15 (1)	3.0265 (12)	175 (1)
C1—H1c⋯O1i	0.98	2.55	3.4972 (18)	163
C1—H1a⋯Cl1ii	0.98	2.83	3.7592 (15)	159
C7—H7⋯Cl1iii	0.95	2.82	3.6803 (14)	152
C8—H8⋯Cl1iv	0.95	2.81	3.7329 (14)	165
C18—H18⋯Cl1v	0.95	2.74	3.6175 (14)	154

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