Oxomemazine hydro­chloride

Siddegowda, M.S.; Butcher, R.J.; Akkurt, M.; Yathirajan, H.S.; Ramesh, A.R.

doi:10.1107/S1600536811025372

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o1875

doi:10.1107/S1600536811025372

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Oxomemazine hydrochloride

M. S. Siddegowda,^a Ray J. Butcher,^b Mehmet Akkurt,^c ^* H. S. Yathirajan ^a and A. R. Ramesh ^d

^aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, ^bDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA, ^cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, and ^dR. L. Fine Chem, Bangalore 560 064, India
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 21 June 2011; accepted 28 June 2011; online 2 July 2011)

In the title compound [systematic name: 3-(5,5-dioxophenothiazin-10-yl)-N,N,2-trimethylpropanaminium chloride], C₁₈H₂₃N₂O₂S⁺·Cl⁻, the dihedral angle between the two outer aromatic rings of the phenothiazine unit is 30.5 (2)°. In the crystal, the components are linked by N—H⋯Cl and C—H⋯Cl hydrogen bonds and C—H⋯π interactions.

Related literature

For background to oxomemazine, see: Amin et al. (2008 ); El-Didamony, (2005 ). For related structures, see: Harrison et al. (2007 ); Jasinski et al. (2011 ).

Experimental

Crystal data

C₁₈H₂₃N₂O₂S⁺·Cl⁻
M_r = 366.90
Triclinic, $[P \overline 1]$
a = 7.6364 (7) Å
b = 10.4177 (9) Å
c = 12.4732 (10) Å
α = 103.478 (7)°
β = 90.624 (7)°
γ = 109.852 (8)°
V = 903.21 (15) Å³
Z = 2
Cu Kα radiation
μ = 3.06 mm⁻¹
T = 295 K
0.32 × 0.25 × 0.24 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction: refined from ΔF [XABS2 (Parkin et al., 1995 ) in WinGX (Farrugia (1999 )]T_min = 0.441, T_max = 0.528
6466 measured reflections
3598 independent reflections
3120 reflections with I > 2σ(I)
R_int = 0.0422

Refinement

R[F² > 2σ(F²)] = 0.079
wR(F²) = 0.229
S = 1.09
3598 reflections
221 parameters
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.55 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯Cl1	0.91	2.18	3.027 (4)	155
C13—H13A⋯Cl1ⁱ	0.97	2.80	3.608 (4)	141
C13—H13B⋯Cl1	0.97	2.76	3.692 (4)	161
C17—H17B⋯Cg2ⁱⁱ	0.96	2.62	3.559 (6)	166
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); 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, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811025372/hb5925sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811025372/hb5925Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811025372/hb5925Isup3.cml

checkCIF report

Comment top

Oxomemazine is an antihistamine and anticholinergic of the phenothiazine chemical class used for the treatment of cough. The extractive spectrophotometric methods for the determination of oxomemazine hydrochloride in bulk and pharmaceutical formulations using some organic dyes is described (El-Didamony, 2005; Amin et al., 2008). The crystal structures of dioxopromethazinium picrate (Harrison et al., 2007) and 1-(10H-phenothiazin-2-yl)ethanone (Jasinski et al., 2011) have been reported. We now report the crystal structure of the title compound, (I).

In the molecule of (I), (Fig. 1), the dihedral angle between the two aromatic rings of the phenothiazine unit is 30.5 (2)°. All bond lengths and angles in (I) are normal. In the crystal structure, N—H···Cl, C—H···Cl hydrogen bonds (Table 1, Fig. 2) and C—H···π interactions help to establish the packing of (I).

Related literature top

For background to oxomemazine, see: Amin et al. (2008); El-Didamony, (2005). For related structures, see: Harrison et al. (2007); Jasinski et al. (2011).

Experimental top

The title compound was obtained as a gift sample from R. L. Fine Chem., Bangalore, India. X-ray quality crystals were obtained from a 1:1 mixture of dimethylformamide and ethanol by slow evaporation (m.p.: 520–523 K).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); 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, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of (I) showing displacement ellipsoids for non-H atoms drawn at the 30% probability level.
	Fig. 2. A view of the crystal packing and hydrogen bonding of (I) shown down the a axis.

3-(5,5-dioxophenothiazin-10-yl)-N,N,2-trimethylpropanaminium chloride top

Crystal data top

C₁₈H₂₃N₂O₂S⁺·Cl⁻	Z = 2
M_r = 366.90	F(000) = 388
Triclinic, P1	D_x = 1.349 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 7.6364 (7) Å	Cell parameters from 3224 reflections
b = 10.4177 (9) Å	θ = 4.7–75.0°
c = 12.4732 (10) Å	µ = 3.06 mm⁻¹
α = 103.478 (7)°	T = 295 K
β = 90.624 (7)°	Prism, colourless
γ = 109.852 (8)°	0.32 × 0.25 × 0.24 mm
V = 903.21 (15) Å³

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	3598 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3120 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.074
Detector resolution: 10.5081 pixels mm^-1	θ_max = 75.8°, θ_min = 4.7°
ω scans	h = −9→9
Absorption correction: part of the refinement model (ΔF) [XABS2 (Parkin et al., 1995) in the WinGX (Farrugia (1999).	k = −12→12
T_min = 0.441, T_max = 0.528	l = 0→15
6466 measured reflections

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)] = 0.079	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.229	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.1168P)² + 1.2778P] where P = (F_o² + 2F_c²)/3
3598 reflections	(Δ/σ)_max < 0.001
221 parameters	Δρ_max = 0.48 e Å⁻³
0 restraints	Δρ_min = −0.55 e Å⁻³

Crystal data top

C₁₈H₂₃N₂O₂S⁺·Cl⁻	γ = 109.852 (8)°
M_r = 366.90	V = 903.21 (15) Å³
Triclinic, P1	Z = 2
a = 7.6364 (7) Å	Cu Kα radiation
b = 10.4177 (9) Å	µ = 3.06 mm⁻¹
c = 12.4732 (10) Å	T = 295 K
α = 103.478 (7)°	0.32 × 0.25 × 0.24 mm
β = 90.624 (7)°

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	3598 independent reflections
Absorption correction: part of the refinement model (ΔF) [XABS2 (Parkin et al., 1995) in the WinGX (Farrugia (1999).	3120 reflections with I > 2σ(I)
T_min = 0.441, T_max = 0.528	R_int = 0.074
6466 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.079	0 restraints
wR(F²) = 0.229	H-atom parameters constrained
S = 1.09	Δρ_max = 0.48 e Å⁻³
3598 reflections	Δρ_min = −0.55 e Å⁻³
221 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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
S1	0.59166 (14)	0.20629 (10)	0.95014 (7)	0.0449 (3)
O1	0.5426 (5)	0.1883 (4)	1.0580 (2)	0.0663 (10)
O2	0.7225 (4)	0.1441 (3)	0.9009 (3)	0.0587 (10)
N1	0.5526 (5)	0.3244 (3)	0.7585 (3)	0.0434 (9)
N2	0.5857 (5)	0.2792 (4)	0.3894 (3)	0.0448 (10)
C1	0.4037 (5)	0.2045 (4)	0.7654 (3)	0.0401 (10)
C2	0.2542 (6)	0.1382 (4)	0.6801 (3)	0.0492 (11)
C3	0.1031 (6)	0.0237 (5)	0.6921 (4)	0.0552 (14)
C4	0.0937 (6)	−0.0284 (5)	0.7851 (4)	0.0590 (14)
C5	0.2388 (6)	0.0333 (4)	0.8684 (4)	0.0511 (12)
C6	0.3941 (5)	0.1471 (4)	0.8570 (3)	0.0412 (10)
C7	0.6735 (5)	0.3847 (4)	0.9521 (3)	0.0412 (11)
C8	0.7662 (6)	0.4839 (4)	1.0502 (3)	0.0495 (11)
C9	0.8514 (6)	0.6230 (5)	1.0501 (4)	0.0547 (12)
C10	0.8428 (6)	0.6621 (4)	0.9525 (4)	0.0540 (11)
C11	0.7472 (6)	0.5662 (4)	0.8560 (4)	0.0503 (12)
C12	0.6580 (5)	0.4229 (4)	0.8529 (3)	0.0400 (10)
C13	0.5914 (6)	0.3516 (4)	0.6489 (3)	0.0443 (11)
C14	0.6707 (6)	0.2476 (5)	0.5775 (3)	0.0494 (12)
C15	0.8375 (9)	0.2381 (8)	0.6378 (5)	0.084 (2)
C16	0.7363 (6)	0.2971 (5)	0.4743 (3)	0.0507 (14)
C17	0.4856 (8)	0.1292 (5)	0.3288 (5)	0.0709 (17)
C18	0.6669 (8)	0.3653 (6)	0.3094 (4)	0.0664 (16)
Cl1	0.22428 (14)	0.32837 (11)	0.44260 (9)	0.0524 (3)
H2A	0.25720	0.17110	0.61670	0.0590*
H2B	0.50060	0.31300	0.42450	0.0540*
H3A	0.00520	−0.01930	0.63590	0.0660*
H4A	−0.00980	−0.10460	0.79140	0.0710*
H5A	0.23360	−0.00030	0.93150	0.0610*
H8A	0.77010	0.45550	1.11530	0.0600*
H9A	0.91380	0.68960	1.11470	0.0650*
H10A	0.90310	0.75580	0.95170	0.0650*
H11A	0.74180	0.59690	0.79220	0.0600*
H13A	0.68010	0.44670	0.65870	0.0530*
H13B	0.47660	0.34550	0.61050	0.0530*
H14A	0.57280	0.15410	0.55540	0.0590*
H15A	0.79770	0.19790	0.69920	0.1250*
H15B	0.92950	0.33080	0.66460	0.1250*
H15C	0.89070	0.17960	0.58800	0.1250*
H16A	0.81350	0.39620	0.49720	0.0610*
H16B	0.81480	0.24610	0.44000	0.0610*
H17A	0.41330	0.07910	0.37840	0.1060*
H17B	0.57500	0.08670	0.30100	0.1060*
H17C	0.40390	0.12520	0.26810	0.1060*
H18A	0.72400	0.46260	0.34880	0.0990*
H18B	0.56930	0.35570	0.25570	0.0990*
H18C	0.75940	0.33290	0.27250	0.0990*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0587 (6)	0.0433 (5)	0.0309 (5)	0.0145 (4)	−0.0028 (4)	0.0112 (3)
O1	0.095 (2)	0.0633 (19)	0.0316 (15)	0.0125 (17)	−0.0023 (15)	0.0187 (13)
O2	0.0562 (17)	0.0536 (17)	0.069 (2)	0.0230 (14)	−0.0042 (15)	0.0155 (15)
N1	0.0551 (18)	0.0425 (16)	0.0297 (15)	0.0128 (14)	0.0014 (13)	0.0101 (12)
N2	0.0564 (18)	0.0517 (18)	0.0292 (15)	0.0247 (15)	0.0070 (13)	0.0070 (12)
C1	0.0470 (19)	0.0416 (18)	0.0321 (17)	0.0179 (15)	0.0046 (14)	0.0063 (14)
C2	0.058 (2)	0.053 (2)	0.0380 (19)	0.0230 (18)	−0.0036 (17)	0.0090 (16)
C3	0.048 (2)	0.051 (2)	0.058 (3)	0.0115 (17)	−0.0092 (18)	0.0070 (19)
C4	0.052 (2)	0.050 (2)	0.068 (3)	0.0080 (18)	0.001 (2)	0.017 (2)
C5	0.056 (2)	0.047 (2)	0.048 (2)	0.0138 (17)	0.0061 (18)	0.0143 (17)
C6	0.0487 (19)	0.0388 (17)	0.0350 (18)	0.0151 (15)	0.0026 (14)	0.0075 (14)
C7	0.052 (2)	0.0384 (18)	0.0298 (17)	0.0134 (15)	0.0039 (14)	0.0059 (13)
C8	0.059 (2)	0.052 (2)	0.0287 (18)	0.0134 (18)	−0.0002 (16)	0.0028 (15)
C9	0.062 (2)	0.050 (2)	0.041 (2)	0.0147 (19)	0.0038 (18)	−0.0018 (17)
C10	0.062 (2)	0.0389 (19)	0.052 (2)	0.0098 (17)	0.0027 (19)	0.0066 (17)
C11	0.062 (2)	0.044 (2)	0.044 (2)	0.0167 (18)	0.0038 (17)	0.0124 (16)
C12	0.0455 (18)	0.0410 (18)	0.0327 (17)	0.0156 (15)	0.0041 (14)	0.0074 (14)
C13	0.058 (2)	0.048 (2)	0.0305 (17)	0.0195 (17)	0.0049 (15)	0.0152 (15)
C14	0.057 (2)	0.061 (2)	0.040 (2)	0.0286 (19)	0.0092 (17)	0.0195 (18)
C15	0.082 (3)	0.145 (6)	0.068 (3)	0.072 (4)	0.026 (3)	0.060 (4)
C16	0.052 (2)	0.071 (3)	0.037 (2)	0.029 (2)	0.0118 (16)	0.0172 (18)
C17	0.080 (3)	0.054 (3)	0.067 (3)	0.022 (2)	−0.006 (3)	−0.004 (2)
C18	0.086 (3)	0.084 (3)	0.040 (2)	0.036 (3)	0.020 (2)	0.026 (2)
Cl1	0.0493 (5)	0.0565 (6)	0.0514 (6)	0.0189 (4)	0.0047 (4)	0.0133 (4)

Geometric parameters (Å, º) top

S1—O1	1.438 (3)	C14—C15	1.516 (9)
S1—O2	1.436 (3)	C14—C16	1.524 (6)
S1—C6	1.733 (4)	C2—H2A	0.9300
S1—C7	1.742 (4)	C3—H3A	0.9300
N1—C1	1.396 (5)	C4—H4A	0.9300
N1—C12	1.394 (5)	C5—H5A	0.9300
N1—C13	1.473 (5)	C8—H8A	0.9300
N2—C16	1.488 (6)	C9—H9A	0.9300
N2—C17	1.491 (7)	C10—H10A	0.9300
N2—C18	1.496 (7)	C11—H11A	0.9300
N2—H2B	0.9100	C13—H13A	0.9700
C1—C6	1.400 (5)	C13—H13B	0.9700
C1—C2	1.417 (6)	C14—H14A	0.9800
C2—C3	1.389 (7)	C15—H15A	0.9600
C3—C4	1.384 (7)	C15—H15B	0.9600
C4—C5	1.379 (7)	C15—H15C	0.9600
C5—C6	1.400 (6)	C16—H16A	0.9700
C7—C8	1.400 (5)	C16—H16B	0.9700
C7—C12	1.401 (5)	C17—H17A	0.9600
C8—C9	1.373 (6)	C17—H17B	0.9600
C9—C10	1.378 (7)	C17—H17C	0.9600
C10—C11	1.380 (7)	C18—H18A	0.9600
C11—C12	1.406 (6)	C18—H18B	0.9600
C13—C14	1.530 (6)	C18—H18C	0.9600

O1—S1—O2	117.1 (2)	C3—C4—H4A	120.00
O1—S1—C6	111.1 (2)	C5—C4—H4A	120.00
O1—S1—C7	110.2 (2)	C4—C5—H5A	120.00
O2—S1—C6	108.2 (2)	C6—C5—H5A	120.00
O2—S1—C7	108.99 (19)	C7—C8—H8A	120.00
C6—S1—C7	99.90 (19)	C9—C8—H8A	120.00
C1—N1—C12	121.7 (3)	C8—C9—H9A	121.00
C1—N1—C13	118.9 (3)	C10—C9—H9A	121.00
C12—N1—C13	119.3 (3)	C9—C10—H10A	119.00
C16—N2—C17	113.2 (4)	C11—C10—H10A	119.00
C16—N2—C18	109.4 (4)	C10—C11—H11A	119.00
C17—N2—C18	110.1 (4)	C12—C11—H11A	120.00
C16—N2—H2B	108.00	N1—C13—H13A	109.00
C17—N2—H2B	108.00	N1—C13—H13B	109.00
C18—N2—H2B	108.00	C14—C13—H13A	109.00
N1—C1—C2	120.7 (3)	C14—C13—H13B	109.00
N1—C1—C6	121.7 (4)	H13A—C13—H13B	108.00
C2—C1—C6	117.6 (4)	C13—C14—H14A	109.00
C1—C2—C3	119.4 (4)	C15—C14—H14A	109.00
C2—C3—C4	122.0 (4)	C16—C14—H14A	109.00
C3—C4—C5	119.6 (5)	C14—C15—H15A	109.00
C4—C5—C6	119.4 (4)	C14—C15—H15B	109.00
S1—C6—C1	118.3 (3)	C14—C15—H15C	110.00
S1—C6—C5	119.3 (3)	H15A—C15—H15B	109.00
C1—C6—C5	122.0 (4)	H15A—C15—H15C	109.00
C8—C7—C12	122.2 (4)	H15B—C15—H15C	110.00
S1—C7—C8	119.0 (3)	N2—C16—H16A	108.00
S1—C7—C12	118.6 (3)	N2—C16—H16B	108.00
C7—C8—C9	119.9 (4)	C14—C16—H16A	108.00
C8—C9—C10	118.8 (4)	C14—C16—H16B	108.00
C9—C10—C11	121.9 (4)	H16A—C16—H16B	107.00
C10—C11—C12	120.9 (4)	N2—C17—H17A	109.00
N1—C12—C7	121.2 (4)	N2—C17—H17B	110.00
N1—C12—C11	122.5 (4)	N2—C17—H17C	110.00
C7—C12—C11	116.2 (4)	H17A—C17—H17B	109.00
N1—C13—C14	112.6 (3)	H17A—C17—H17C	109.00
C13—C14—C15	112.2 (4)	H17B—C17—H17C	109.00
C13—C14—C16	109.1 (4)	N2—C18—H18A	109.00
C15—C14—C16	107.5 (4)	N2—C18—H18B	109.00
N2—C16—C14	115.8 (4)	N2—C18—H18C	109.00
C1—C2—H2A	120.00	H18A—C18—H18B	109.00
C3—C2—H2A	120.00	H18A—C18—H18C	110.00
C2—C3—H3A	119.00	H18B—C18—H18C	110.00
C4—C3—H3A	119.00

O1—S1—C6—C1	154.8 (3)	C6—C1—C2—C3	2.2 (6)
O2—S1—C6—C1	−75.4 (4)	N1—C1—C2—C3	−176.5 (4)
C7—S1—C6—C1	38.5 (4)	N1—C1—C6—C5	175.2 (4)
O1—S1—C6—C5	−32.5 (4)	C2—C1—C6—S1	169.0 (3)
O2—S1—C6—C5	97.4 (4)	C2—C1—C6—C5	−3.5 (6)
C7—S1—C6—C5	−148.7 (3)	C1—C2—C3—C4	−0.1 (7)
O1—S1—C7—C8	30.5 (4)	C2—C3—C4—C5	−0.8 (7)
O2—S1—C7—C8	−99.3 (4)	C3—C4—C5—C6	−0.5 (7)
C6—S1—C7—C8	147.4 (4)	C4—C5—C6—C1	2.7 (7)
O1—S1—C7—C12	−154.8 (3)	C4—C5—C6—S1	−169.7 (4)
O2—S1—C7—C12	75.5 (4)	S1—C7—C12—C11	−172.2 (3)
C6—S1—C7—C12	−37.8 (4)	S1—C7—C12—N1	10.6 (5)
C12—N1—C13—C14	113.2 (4)	C12—C7—C8—C9	−2.4 (7)
C13—N1—C1—C2	−22.4 (6)	S1—C7—C8—C9	172.2 (4)
C12—N1—C1—C6	−24.9 (6)	C8—C7—C12—C11	2.4 (6)
C12—N1—C1—C2	153.8 (4)	C8—C7—C12—N1	−174.9 (4)
C1—N1—C13—C14	−70.6 (5)	C7—C8—C9—C10	0.3 (7)
C13—N1—C12—C7	−158.2 (4)	C8—C9—C10—C11	1.7 (7)
C13—N1—C1—C6	159.0 (4)	C9—C10—C11—C12	−1.6 (7)
C1—N1—C12—C7	25.7 (6)	C10—C11—C12—C7	−0.4 (6)
C1—N1—C12—C11	−151.4 (4)	C10—C11—C12—N1	176.8 (4)
C13—N1—C12—C11	24.8 (6)	N1—C13—C14—C15	−51.8 (6)
C18—N2—C16—C14	165.0 (4)	N1—C13—C14—C16	−170.8 (4)
C17—N2—C16—C14	−71.7 (5)	C15—C14—C16—N2	165.3 (4)
N1—C1—C6—S1	−12.3 (5)	C13—C14—C16—N2	−72.9 (5)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···Cl1	0.91	2.18	3.027 (4)	155
C13—H13A···Cl1ⁱ	0.97	2.80	3.608 (4)	141
C13—H13B···Cl1	0.97	2.76	3.692 (4)	161
C17—H17B···Cg2ⁱⁱ	0.96	2.62	3.559 (6)	166

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

Experimental details

Crystal data
Chemical formula	C₁₈H₂₃N₂O₂S⁺·Cl⁻
M_r	366.90
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	7.6364 (7), 10.4177 (9), 12.4732 (10)
α, β, γ (°)	103.478 (7), 90.624 (7), 109.852 (8)
V (Å³)	903.21 (15)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	3.06
Crystal size (mm)	0.32 × 0.25 × 0.24

Data collection
Diffractometer	Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction	Part of the refinement model (ΔF) [XABS2 (Parkin et al., 1995) in the WinGX (Farrugia (1999).
T_min, T_max	0.441, 0.528
No. of measured, independent and observed [I > 2σ(I)] reflections	6466, 3598, 3120
R_int	0.074
(sin θ/λ)_max (Å⁻¹)	0.629

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.079, 0.229, 1.09
No. of reflections	3598
No. of parameters	221
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.55

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···Cl1	0.91	2.18	3.027 (4)	155
C13—H13A···Cl1ⁱ	0.97	2.80	3.608 (4)	141
C13—H13B···Cl1	0.97	2.76	3.692 (4)	161
C17—H17B···Cg2ⁱⁱ	0.96	2.62	3.559 (6)	166

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

Acknowledgements

MSS thanks the University of Mysore for research facilities and R. L. Fine Chem., Bangalore, India, for the gift sample. RJB acknowledges the NSF–MRI program (grant No. CHE1039027) for funds to purchase the X-ray diffractometer.

References

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