3-Acetyl-2,4-di-methyl-quinolin-1-ium chloride.

In the title salt, C13H14NO(+)·Cl(-), the dihedral angle between the fused ring system (r.m.s. deviation = 0.039 Å) and the attached aldehyde group is 75.27 (16)°. In the crystal, the cation and anion are linked by an N-H⋯Cl hydrogen bond and the resulting pairs are connected into four-ion aggregates by π-π inter-actions between the C6 and pyridinium rings [3.6450 (9) Å] of inversion-related quinolinium residues.

Related literature

For background details and biological applications of quinoline and n class="Chemical">quinoline chalcones, see: Joshi et al. (2011 ▶); Prasath et al. (2013a ▶). For a related structure, see: Prasath et al. (2013b ▶).

Experimental

Crystal data

C13H14NO+·Cl−

M = 235.70

Orthorhombic,

a = 12.8221 (6) Å

b = 10.7281 (4) Å

c = 16.3785 (6) Å

V = 2252.97 (16) Å3

Z = 8

Mo Kα radiation

μ = 0.32 mm−1

T = 100 K

0.50 × 0.40 × 0.30 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013 ▶) T min = 0.956, T max = 1.000

8404 measured reflections

2597 independent reflections

2207 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.099

S = 1.04

2597 reflections

152 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CrysAlis PRO (Agilent, 2013 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681301684X/hb7097sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681301684X/hb7097Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681301684X/hb7097Isup3.cml

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

C13H14NO+·Cl−	F(000) = 992
Mr = 235.70	Dx = 1.390 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3252 reflections
a = 12.8221 (6) Å	θ = 3.0–27.5°
b = 10.7281 (4) Å	µ = 0.32 mm−1
c = 16.3785 (6) Å	T = 100 K
V = 2252.97 (16) Å3	Block, yellow
Z = 8	0.50 × 0.40 × 0.30 mm

Agilent SuperNova Dual diffractometer with an Atlas detector	2597 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2207 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.030
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 3.0°
ω scan	h = −11→16
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −13→10
Tmin = 0.956, Tmax = 1.000	l = −19→21
8404 measured reflections

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0514P)2 + 0.7427P] where P = (Fo2 + 2Fc2)/3
2597 reflections	(Δ/σ)max < 0.001
152 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

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	0.38171 (3)	0.29410 (3)	0.31279 (2)	0.01712 (13)
O1	0.78490 (9)	0.68933 (10)	0.36335 (7)	0.0257 (3)
N1	0.56888 (10)	0.39336 (11)	0.40603 (7)	0.0127 (3)
H1	0.5145 (17)	0.3655 (19)	0.3755 (12)	0.035 (5)*
C1	0.56522 (12)	0.36700 (12)	0.48826 (8)	0.0130 (3)
C2	0.47740 (12)	0.30581 (13)	0.52035 (8)	0.0156 (3)
H2	0.4216	0.2811	0.4858	0.019*
C3	0.47406 (13)	0.28251 (13)	0.60294 (9)	0.0177 (3)
H3	0.4141	0.2441	0.6260	0.021*
C4	0.55806 (13)	0.31479 (13)	0.65333 (9)	0.0185 (3)
H4	0.5555	0.2950	0.7098	0.022*
C5	0.64371 (13)	0.37435 (14)	0.62260 (8)	0.0174 (3)
H5	0.6999	0.3956	0.6577	0.021*
C6	0.64893 (12)	0.40465 (13)	0.53813 (8)	0.0140 (3)
C7	0.73191 (11)	0.47481 (13)	0.50274 (8)	0.0139 (3)
C8	0.81628 (12)	0.52547 (14)	0.55698 (9)	0.0192 (3)
H8A	0.8670	0.5715	0.5239	0.029*
H8B	0.8515	0.4564	0.5848	0.029*
H8C	0.7855	0.5815	0.5976	0.029*
C9	0.72892 (11)	0.49922 (13)	0.41992 (8)	0.0134 (3)
C10	0.64623 (11)	0.45412 (12)	0.37091 (8)	0.0125 (3)
C11	0.64361 (12)	0.47075 (13)	0.28065 (8)	0.0159 (3)
H11A	0.5797	0.4334	0.2587	0.024*
H11B	0.7045	0.4300	0.2562	0.024*
H11C	0.6449	0.5599	0.2676	0.024*
C12	0.80915 (12)	0.58304 (13)	0.37971 (8)	0.0155 (3)
C13	0.91308 (13)	0.52994 (14)	0.35969 (9)	0.0205 (3)
H13A	0.9622	0.5978	0.3485	0.031*
H13B	0.9072	0.4764	0.3114	0.031*
H13C	0.9384	0.4806	0.4060	0.031*

	U11	U22	U33	U12	U13	U23
Cl1	0.0144 (2)	0.0191 (2)	0.01791 (19)	−0.00141 (14)	−0.00107 (14)	−0.00348 (12)
O1	0.0198 (6)	0.0158 (5)	0.0415 (6)	−0.0027 (5)	−0.0034 (5)	0.0074 (5)
N1	0.0120 (6)	0.0124 (5)	0.0138 (5)	0.0001 (5)	−0.0011 (5)	−0.0007 (4)
C1	0.0140 (7)	0.0103 (6)	0.0148 (6)	0.0020 (5)	0.0018 (6)	−0.0002 (5)
C2	0.0150 (8)	0.0120 (6)	0.0197 (7)	0.0007 (6)	0.0010 (6)	−0.0012 (5)
C3	0.0186 (8)	0.0133 (6)	0.0211 (7)	0.0005 (6)	0.0071 (6)	0.0020 (5)
C4	0.0247 (9)	0.0154 (6)	0.0153 (6)	0.0041 (6)	0.0035 (7)	0.0023 (5)
C5	0.0206 (8)	0.0171 (7)	0.0146 (6)	0.0029 (6)	−0.0016 (6)	0.0003 (5)
C6	0.0145 (7)	0.0125 (6)	0.0150 (6)	0.0022 (6)	0.0005 (6)	−0.0012 (5)
C7	0.0129 (7)	0.0127 (6)	0.0162 (6)	0.0030 (6)	−0.0006 (6)	−0.0019 (5)
C8	0.0168 (8)	0.0247 (8)	0.0162 (6)	−0.0040 (7)	−0.0024 (6)	−0.0006 (6)
C9	0.0124 (8)	0.0121 (6)	0.0157 (6)	0.0014 (5)	0.0001 (6)	−0.0006 (5)
C10	0.0122 (7)	0.0111 (6)	0.0142 (6)	0.0020 (6)	−0.0004 (5)	−0.0004 (5)
C11	0.0168 (8)	0.0177 (7)	0.0132 (6)	−0.0016 (6)	−0.0005 (6)	0.0008 (5)
C12	0.0160 (8)	0.0174 (7)	0.0131 (6)	−0.0038 (6)	−0.0033 (6)	−0.0005 (5)
C13	0.0173 (8)	0.0192 (7)	0.0249 (7)	−0.0023 (6)	0.0036 (7)	0.0023 (6)

O1—C12	1.2119 (18)	C7—C9	1.3821 (18)
N1—C10	1.3188 (19)	C7—C8	1.502 (2)
N1—C1	1.3769 (17)	C8—H8A	0.9800
N1—H1	0.91 (2)	C8—H8B	0.9800
C1—C2	1.405 (2)	C8—H8C	0.9800
C1—C6	1.408 (2)	C9—C10	1.415 (2)
C2—C3	1.3762 (19)	C9—C12	1.517 (2)
C2—H2	0.9500	C10—C11	1.4894 (18)
C3—C4	1.400 (2)	C11—H11A	0.9800
C3—H3	0.9500	C11—H11B	0.9800
C4—C5	1.367 (2)	C11—H11C	0.9800
C4—H4	0.9500	C12—C13	1.486 (2)
C5—C6	1.4228 (18)	C13—H13A	0.9800
C5—H5	0.9500	C13—H13B	0.9800
C6—C7	1.426 (2)	C13—H13C	0.9800
C10—N1—C1	123.63 (13)	H8A—C8—H8B	109.5
C10—N1—H1	120.0 (12)	C7—C8—H8C	109.5
C1—N1—H1	116.4 (12)	H8A—C8—H8C	109.5
N1—C1—C2	119.28 (13)	H8B—C8—H8C	109.5
N1—C1—C6	118.85 (13)	C7—C9—C10	120.84 (13)
C2—C1—C6	121.86 (12)	C7—C9—C12	121.31 (13)
C3—C2—C1	118.51 (14)	C10—C9—C12	117.68 (12)
C3—C2—H2	120.7	N1—C10—C9	119.01 (12)
C1—C2—H2	120.7	N1—C10—C11	118.37 (12)
C2—C3—C4	120.69 (14)	C9—C10—C11	122.61 (13)
C2—C3—H3	119.7	C10—C11—H11A	109.5
C4—C3—H3	119.7	C10—C11—H11B	109.5
C5—C4—C3	121.10 (13)	H11A—C11—H11B	109.5
C5—C4—H4	119.4	C10—C11—H11C	109.5
C3—C4—H4	119.4	H11A—C11—H11C	109.5
C4—C5—C6	120.19 (14)	H11B—C11—H11C	109.5
C4—C5—H5	119.9	O1—C12—C13	122.82 (14)
C6—C5—H5	119.9	O1—C12—C9	118.68 (14)
C1—C6—C7	118.97 (12)	C13—C12—C9	118.47 (12)
C1—C6—C5	117.56 (13)	C12—C13—H13A	109.5
C7—C6—C5	123.42 (13)	C12—C13—H13B	109.5
C9—C7—C6	118.56 (13)	H13A—C13—H13B	109.5
C9—C7—C8	122.14 (13)	C12—C13—H13C	109.5
C6—C7—C8	119.21 (12)	H13A—C13—H13C	109.5
C7—C8—H8A	109.5	H13B—C13—H13C	109.5
C7—C8—H8B	109.5
C10—N1—C1—C2	177.60 (13)	C5—C6—C7—C8	−3.1 (2)
C10—N1—C1—C6	−1.1 (2)	C6—C7—C9—C10	−0.9 (2)
N1—C1—C2—C3	−178.66 (12)	C8—C7—C9—C10	−177.57 (13)
C6—C1—C2—C3	0.0 (2)	C6—C7—C9—C12	174.34 (13)
C1—C2—C3—C4	−2.4 (2)	C8—C7—C9—C12	−2.3 (2)
C2—C3—C4—C5	2.5 (2)	C1—N1—C10—C9	−2.3 (2)
C3—C4—C5—C6	−0.1 (2)	C1—N1—C10—C11	176.77 (12)
N1—C1—C6—C7	3.45 (19)	C7—C9—C10—N1	3.3 (2)
C2—C1—C6—C7	−175.19 (13)	C12—C9—C10—N1	−172.12 (12)
N1—C1—C6—C5	−179.02 (12)	C7—C9—C10—C11	−175.71 (13)
C2—C1—C6—C5	2.3 (2)	C12—C9—C10—C11	8.8 (2)
C4—C5—C6—C1	−2.3 (2)	C7—C9—C12—O1	−101.78 (17)
C4—C5—C6—C7	175.13 (13)	C10—C9—C12—O1	73.64 (18)
C1—C6—C7—C9	−2.4 (2)	C7—C9—C12—C13	80.14 (17)
C5—C6—C7—C9	−179.80 (13)	C10—C9—C12—C13	−104.45 (15)
C1—C6—C7—C8	174.32 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl1	0.91 (2)	2.13 (2)	3.0374 (13)	175.4 (17)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Cl1	0.91 (2)	2.13 (2)	3.0374 (13)	175.4 (17)