3-Acetyl-6-chloro-2-methyl-4-phenyl­quinolinium hydrogen sulfate

Loh, W.-S.; Fun, H.-K.; Sarveswari, S.; Vijayakumar, V.; Reddy, B.P.

doi:10.1107/S1600536809048934

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Pages o3144-o3145

doi:10.1107/S1600536809048934

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3-Acetyl-6-chloro-2-methyl-4-phenylquinolinium hydrogen sulfate

Wan-Sin Loh,^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 Science, VIT University, Vellore-632 014, India
^*Correspondence e-mail: hkfun@usm.my

(Received 13 November 2009; accepted 17 November 2009; online 21 November 2009)

In the title salt, C₁₈H₁₅ClNO⁺·HSO₄⁻, 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 intermolecular O—H⋯O hydrogen bonds links two hydrogen sulfate anions into a dimer, generating a R₂²(8) ring motif. Intermolecular 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 interactions

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_r = 393.83
Triclinic, $[P \overline 1]$
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 (SADABS; 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[F² > 2σ(F²)] = 0.044
wR(F²) = 0.100
S = 1.05
5036 reflections
299 parameters
All H-atom parameters refined
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.46 e Å⁻³

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⋯O4^iv	0.95 (3)	2.55 (3)	3.332 (2)	139 (2)
C12—H12A⋯Cg1^v	0.95 (2)	2.74 (2)	3.5884 (18)	149.1 (14)
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) -x, -y+1, -z+1; (iii) x, y+1, z; (iv) x+1, y, z; (v) -x+1, -y+2, -z+2. Cg1 is the centroid of the C1–C6 ring.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809048934/tk2576sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809048934/tk2576Isup2.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 have found attractive applications as pharmaceuticals, agrochemicals and as synthetic building blocks (Maguire et al., 1994; Kalluraya & Sreenivasa, 1998; Roma et al., 2000; Chen et al., 2001). The 3-acetyl-6-chloro-2-methyl-4-phenylquinoline has been synthesized using the method available in the literature (Fun et al., 2009), and then converted into the title salt, (I).

The asymmetric unit of (I), Fig. 1, contains a 3-acetyl-6-chloro-2-methyl-4-phenylquinolinium cation and a hydrogen sulfate anion. One proton is transferred from the hydroxyl group of hydrogen sulfate to the atom N1 of 3-acetyl-6-chloro-2-methyl-4-phenylquinoline during crystallisation resulting in the formation of salt, (I). The quinolinium ring system (C1–C9/N1) is approximately planar with a maximum deviation of 0.028 (2) Å at atom C7. This mean plane of the quinolinium ring forms a dihedral angle of 78.43 (4)° with the phenyl ring (C10–C15). Bond lengths and angles are comparable to a closely related structure (Fun et al., 2009).

In the crystal packing (Fig. 2), a pair of O2—H1O2···O3 hydrogen bonds link two hydrogen sulfate anions into dimers, generating R₂²(8) ring motifs stacked along a axis (Bernstein et al., 1995). A N1—H1N1—O5 hydrogen bond links the dimer with the quinolinium ring system. The ions are linked into a 3-D network by C5—H5A···O3, C15—H15A···O4 and C16—H16C···O4 contacts. The structure is further stabilized by C—H···π interactions (Table 1), involving C1–C6 (centroid Cg1) ring system.

Related literature top

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). Cg1 is the centroid of the C1–C6 ring.

Experimental top

To a solution of 3-acetyl-6-chloro-2-methyl-4-phenylquinoline (10 ml, 1 M) in ethanol, copper sulfate solution (1 ml, 1 M) and concentrated H₂SO₄ (1 ml) was added and then refluxed for about 10 min. The contents were filtered and kept for 92 h for crystallization.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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 30% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The crystal packing of (I), viewed along the a axis, showing the 3-D network. H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

3-Acetyl-6-chloro-2-methyl-4-phenylquinolinium hydrogen sulfate top

Crystal data top

C₁₈H₁₅ClNO⁺·HSO₄⁻	Z = 2
M_r = 393.83	F(000) = 408
Triclinic, P1	D_x = 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

Data collection top

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

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.100	All H-atom parameters refined
S = 1.05	w = 1/[σ²(F_o²) + (0.0423P)² + 0.5203P] where P = (F_o² + 2F_c²)/3
5036 reflections	(Δ/σ)_max < 0.001
299 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.46 e Å⁻³

Crystal data top

C₁₈H₁₅ClNO⁺·HSO₄⁻	γ = 99.539 (1)°
M_r = 393.83	V = 859.55 (2) Å³
Triclinic, P1	Z = 2
a = 7.3912 (1) Å	Mo Kα radiation
b = 8.8547 (1) Å	µ = 0.37 mm⁻¹
c = 13.3413 (2) Å	T = 100 K
α = 92.485 (1)°	0.28 × 0.18 × 0.11 mm
β = 91.889 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5036 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	4099 reflections with I > 2σ(I)
T_min = 0.902, T_max = 0.960	R_int = 0.036
20789 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.100	All H-atom parameters refined
S = 1.05	Δρ_max = 0.49 e Å⁻³
5036 reflections	Δρ_min = −0.46 e Å⁻³
299 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 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.

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

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O4^iv	0.95 (3)	2.55 (3)	3.332 (2)	139 (2)
C12—H12A···Cg1^v	0.95 (2)	2.74 (2)	3.5884 (18)	149.1 (14)

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x, −y+1, −z+1; (iii) x, y+1, z; (iv) x+1, y, z; (v) −x+1, −y+2, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₅ClNO⁺·HSO₄⁻
M_r	393.83
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.3912 (1), 8.8547 (1), 13.3413 (2)
α, β, γ (°)	92.485 (1), 91.889 (1), 99.539 (1)
V (Å³)	859.55 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.37
Crystal size (mm)	0.28 × 0.18 × 0.11

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.902, 0.960
No. of measured, independent and observed [I > 2σ(I)] reflections	20789, 5036, 4099
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.706

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.100, 1.05
No. of reflections	5036
No. of parameters	299
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.46

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), 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···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···O4^iv	0.95 (3)	2.55 (3)	3.332 (2)	139 (2)
C12—H12A···Cg1^v	0.95 (2)	2.74 (2)	3.5884 (18)	149.1 (14)

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x, −y+1, −z+1; (iii) x, y+1, z; (iv) x+1, y, z; (v) −x+1, −y+2, −z+2.

Footnotes

‡Thomson Reuters ResearcherID: C-7581-2009.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and WSL thank USM for the Research University Golden Goose Grant (1001/PFIZIK/811012). WSL thanks the Malaysian government and USM for the award of the post of Assistant Research Officer under the Research University Golden Goose Grant (1001/PFIZIK/811012). VV is grateful to DST-India for funding through the Young Scientist Scheme (Fast Track Proposal).

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