3-Acetyl-6-chloro-2-methyl-4-phenyl­quinolinium perchlorate

Shahani, T.; Fun, H.-K.; Sarveswari, S.; Vijayakumar, V.; Reddy, B.P.

doi:10.1107/S1600536810012900

organic compounds

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ISSN: 2056-9890

Volume 66| Part 5| May 2010| Pages o1192-o1193

https://doi.org/10.1107/S1600536810012900

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3-Acetyl-6-chloro-2-methyl-4-phenylquinolinium perchlorate

Tara Shahani,^a Hoong-Kun Fun,^a ^*‡ S. Sarveswari,^b V. Vijayakumar ^b and B. Palakshi Reddy ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bOrganic Chemistry Division, School of Advanced Sciences, VIT University, Vellore 632 014, India
^*Correspondence e-mail: hkfun@usm.my

(Received 5 April 2010; accepted 7 April 2010; online 28 April 2010)

In the title molecular salt, C₁₈H₁₅ClNO⁺·ClO₄⁻, the quinolinium 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, intermolecular 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 interactions.

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_r = 396.21
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.031
wR(F²) = 0.108
S = 1.09
7482 reflections
295 parameters
All H-atom parameters refined
Δρ_max = 0.69 e Å⁻³
Δρ_min = −1.00 e Å⁻³

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⋯Cg1^iv	0.981 (17)	2.694 (17)	3.5810 (10)	150.6 (13)
Symmetry codes: (i) -x, -y, -z+1; (ii) x, y-1, z; (iii) x-1, y, z; (iv) -x, -y, -z.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810012900/hb5397sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810012900/hb5397Isup2.hkl

checkCIF report

Comment top

Quinolines and their derivatives are very important compounds because of their wide occurrence in natural products (Morimoto et al., 1991; Michael, 1997), and biologically active compounds (Markees et al., 1970 ; Campbell et al., 1988). A large variety of quinolines have interesting physiological activities and found attractive applications as pharmaceuticals, agrochemicals and as synthetic building blocks, due to their great importance, the synthesis of new derivatives of quinoline remains an active research area (Katritzky & Arend, 1998; Jiang & Si, 2002).

In the title compound (Fig. 1), the asymmetric unit consists one perchlorate anion and one 3-acetyl-6-chloro-2-methyl-4-phenlquineline-1-ium cation. The quinolinium ring system (C1/N1/C2–C9) is approximately planar, with a maximum deviation of 0.027 (1) Å at atom C1. The dihedral angle formed between quinolinium ring system and benzene ring (C10–C15) is 78.46 (3)°. Bond lengths (Allen et al., 1987) and angles are normal and comparable to those related structures (Shahani et al., 2010; Fun et al., 2009; Loh et al., 2010).

In the crystal packing (Fig. 2), intermolecular N1—H1N1···O3, C3—H3A···O2, C15—H15A···O5 and C18—H18B···O5 hydrogen bonds (Table 1) link the molecules into three-dimensional network. This crystal structure is further consolidated by C—H···π interactions involving C10–C15 benzene ring (centroid Cg1).

Related literature top

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 top

A mixture of 3-acetyl-6-chloro-2-methyl-4-phenylquinoline and a catalytic amount of nickel chloride in acid medium was refluxed for about an hour and resultant compound was recrystallized from 3:1 ethanol water to yield colourless blocks of (I).

Structure description top

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).

Computing details top

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).

Figures top

	Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids.
	Fig. 2. The crystal packing of (I), viewed along a axis. H atoms not involved in intermolecular interactions (dashed lines) are omitted for clarity.

3-Acetyl-6-chloro-2-methyl-4-phenylquinolinium perchlorate top

Crystal data top

C₁₈H₁₅ClNO⁺·ClO₄⁻	Z = 2
M_r = 396.21	F(000) = 408
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0636P)² + 0.2949P] where P = (F_o² + 2F_c²)/3
7482 reflections	(Δ/σ)_max < 0.001
295 parameters	Δρ_max = 0.69 e Å⁻³
0 restraints	Δρ_min = −1.00 e Å⁻³

Crystal data top

C₁₈H₁₅ClNO⁺·ClO₄⁻	γ = 99.550 (1)°
M_r = 396.21	V = 858.44 (3) Å³
Triclinic, P1	Z = 2
a = 7.3862 (1) Å	Mo Kα radiation
b = 8.8519 (2) Å	µ = 0.41 mm⁻¹
c = 13.3378 (3) Å	T = 100 K
α = 92.477 (1)°	0.58 × 0.54 × 0.27 mm
β = 91.903 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	7482 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	6933 reflections with I > 2σ(I)
T_min = 0.797, T_max = 0.898	R_int = 0.019
27967 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.108	All H-atom parameters refined
S = 1.09	Δρ_max = 0.69 e Å⁻³
7482 reflections	Δρ_min = −1.00 e Å⁻³
295 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···Cg1^iv	0.981 (17)	2.694 (17)	3.5810 (10)	150.6 (13)

Symmetry codes: (i) −x, −y, −z+1; (ii) x, y−1, z; (iii) x−1, y, z; (iv) −x, −y, −z.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₅ClNO⁺·ClO₄⁻
M_r	396.21
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.3862 (1), 8.8519 (2), 13.3378 (3)
α, β, γ (°)	92.477 (1), 91.903 (1), 99.550 (1)
V (Å³)	858.44 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.41
Crystal size (mm)	0.58 × 0.54 × 0.27

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.797, 0.898
No. of measured, independent and observed [I > 2σ(I)] reflections	27967, 7482, 6933
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.807

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.108, 1.09
No. of reflections	7482
No. of parameters	295
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.69, −1.00

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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···Cg1^iv	0.981 (17)	2.694 (17)	3.5810 (10)	150.6 (13)

Symmetry codes: (i) −x, −y, −z+1; (ii) x, y−1, z; (iii) x−1, y, z; (iv) −x, −y, −z.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

TSH and HKF thank the Universiti Sains Malaysia (USM) for Research University Golden Goose grant No. 1001/PFIZIK/811012. VV is grateful to the DST, India, for funding through the Young Scientist Scheme (Fast Track Proposal).

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