1-Methyl-4-(4-methylstyryl)pyridinium 4-methylbenzenesulfonate

Krishnakumar, M.; Sudhahar, S.; Silambarasan, A.; Chakkaravarthi, G.; Mohankumar, R.

doi:10.1107/S1600536812044509

organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page o3268

doi:10.1107/S1600536812044509

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1-Methyl-4-(4-methylstyryl)pyridinium 4-methylbenzenesulfonate

M. Krishnakumar,^a S. Sudhahar,^a A. Silambarasan,^a G. Chakkaravarthi ^b ^* and R. Mohankumar ^c ^*

^aDepartment of Physics, Presidency College, Chennai 600 005, India, ^bDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, and ^cDepartment of physics, Presidency College, Chennai 600 005, India
^*Correspondence e-mail: chakkaravarthi_2005@yahoo.com, mohan66@hotmail.com

(Received 23 October 2012; accepted 26 October 2012; online 3 November 2012)

In the title salt, C₁₅H₁₆N⁺·C₇H₇O₃S⁻, the dihedral angle between the pyridine and benzene rings of the cation is 5.98 (18)°. In the crystal, adjacent anions and cations are linked by weak non-classical C—H⋯O hydrogen bonds and π–π interactions, with a centroid–centroid distance of 3.749 (2) Å.

Related literature

For molecular compounds with non-linear optical properties, see: Bosshard et al. (1995 ); Nalwa & Miyata (1997 ). For related structures, see: Murugavel et al. (2009 ); Sivakumar et al. (2012 ); Okada et al. (1990 ).

Experimental

Crystal data

C₁₅H₁₆N⁺·C₇H₇O₃S⁻
M_r = 381.48
Monoclinic, P 2₁ /c
a = 9.1380 (6) Å
b = 6.4257 (5) Å
c = 33.884 (2) Å
β = 95.004 (4)°
V = 1982.0 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 295 K
0.28 × 0.22 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.950, T_max = 0.964
18512 measured reflections
4902 independent reflections
3850 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.075
wR(F²) = 0.184
S = 1.13
4902 reflections
247 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O2ⁱ	0.93	2.42	3.273 (4)	152
C14—H14B⋯O1ⁱⁱ	0.96	2.59	3.482 (4)	155
Symmetry codes: (i) x+1, y-1, z; (ii) x, y-1, z.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812044509/rk2384sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812044509/rk2384Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812044509/rk2384Isup3.cml

checkCIF report

Comment top

In continuation of our studies of molecular compounds with non linear optical properties which are known to exhibit applications in optoelectronic and photonic devices (Bosshard et al., 1995; Nalwa & Miyata, 1997), we determined the crystal structure of the title compound I.

The asymmetric unit of I, (Fig. 1), contains C₁₅H₁₆N⁺ cation and C₇H₇O₃S^- anion. The geometric parameters of the title compound are comparable with the similar reported structures: Murugavel et al., 2009; Sivakumar et al., 2012; Okada et al., 1990. The cation is planar - torsion angle about the double bond between the two rings in the cation, C1–C6═C7–C8 is 178.2 (3)°. The benzene ring in the anion is almost planar, with the maximum deviation of 0.003 (3)Å.

In the crystal structure, the adjacent anions and cations are linked by weak non-classical C–H···O H bonds (Table 1 & Fig.2) and π–π interactions - Cg1···Cg2ⁱⁱⁱ = 3.749 (2)Å, where Cg1 and Cg2 are the centroids of the rings (C1-C5/N1) and (C8-C13), respectively. Symmetry code: (iii) x, -y-1/2, z+1/2.

Related literature top

For molecular compounds with non-linear optical properties, see: Bosshard et al. (1995); Nalwa & Miyata (1997). For related structures, see: Murugavel et al. (2009); Sivakumar et al. (2012); Okada et al. (1990).

Experimental top

The title compound was synthesized by the condensation of 4-methyl-N-methyl pyridinium tosylate, which was prepared from 4-picoline (4.65 g, 5 mmol) and methyl p-toluenesulfonate (9.31 g, 5 mmol), and 4-methylbenzaldehyde (6 g, 5 mmol) in the presence of piperidine. The single crystals were grown by slow evaporation method in room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of I with atom labels. Displacement ellipsoids are drawn at 30% probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. The packing of I, viewed down b axis. Intermolecular hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity.

1-Methyl-4-(4-methylstyryl)pyridinium 4-methylbenzenesulfonate top

Crystal data top

C₁₅H₁₆N⁺·C₇H₇O₃S⁻	F(000) = 808
M_r = 381.48	D_x = 1.278 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4112 reflections
a = 9.1380 (6) Å	θ = 2.2–28.4°
b = 6.4257 (5) Å	µ = 0.19 mm⁻¹
c = 33.884 (2) Å	T = 295 K
β = 95.004 (4)°	Block, colourless
V = 1982.0 (2) Å³	0.28 × 0.22 × 0.20 mm
Z = 4

Data collection top

Bruker Kappa APEXII diffractometer	4902 independent reflections
Radiation source: fine-focus sealed tube	3850 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ω– and ϕ–scans	θ_max = 28.4°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.950, T_max = 0.964	k = −8→8
18512 measured reflections	l = −44→45

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)] = 0.075	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.184	H-atom parameters constrained
S = 1.13	w = 1/[σ²(F_o²) + (0.0478P)² + 2.5149P] where P = (F_o² + 2F_c²)/3
4902 reflections	(Δ/σ)_max < 0.001
247 parameters	Δρ_max = 0.57 e Å⁻³
1 restraint	Δρ_min = −0.37 e Å⁻³

Crystal data top

C₁₅H₁₆N⁺·C₇H₇O₃S⁻	V = 1982.0 (2) Å³
M_r = 381.48	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.1380 (6) Å	µ = 0.19 mm⁻¹
b = 6.4257 (5) Å	T = 295 K
c = 33.884 (2) Å	0.28 × 0.22 × 0.20 mm
β = 95.004 (4)°

Data collection top

Bruker Kappa APEXII diffractometer	4902 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3850 reflections with I > 2σ(I)
T_min = 0.950, T_max = 0.964	R_int = 0.031
18512 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.075	1 restraint
wR(F²) = 0.184	H-atom parameters constrained
S = 1.13	Δρ_max = 0.57 e Å⁻³
4902 reflections	Δρ_min = −0.37 e Å⁻³
247 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
C1	0.8177 (3)	0.1727 (5)	0.32460 (9)	0.0480 (7)
C2	0.9323 (3)	0.0485 (6)	0.31430 (10)	0.0586 (9)
H2	1.0286	0.0873	0.3219	0.070*
C3	0.9059 (3)	−0.1293 (6)	0.29319 (10)	0.0557 (8)
H3	0.9848	−0.2100	0.2867	0.067*
C4	0.6546 (3)	−0.0742 (5)	0.29074 (9)	0.0519 (7)
H4	0.5595	−0.1168	0.2826	0.062*
C5	0.6764 (3)	0.1060 (5)	0.31182 (10)	0.0535 (8)
H5	0.5959	0.1851	0.3177	0.064*
C6	0.8525 (4)	0.3602 (6)	0.34869 (10)	0.0581 (8)
H6	0.9514	0.3895	0.3552	0.070*
C7	0.7580 (4)	0.4879 (6)	0.36164 (10)	0.0562 (8)
H7	0.6593	0.4607	0.3545	0.067*
C8	0.7923 (4)	0.6722 (5)	0.38662 (9)	0.0511 (7)
C9	0.6807 (4)	0.8026 (7)	0.39551 (11)	0.0687 (10)
H9	0.5849	0.7725	0.3856	0.082*
C10	0.7073 (5)	0.9779 (7)	0.41889 (13)	0.0780 (12)
H10	0.6288	1.0626	0.4242	0.094*
C11	0.8446 (5)	1.0290 (6)	0.43424 (10)	0.0666 (10)
C12	0.9570 (5)	0.8987 (8)	0.42589 (13)	0.0834 (13)
H12	1.0523	0.9282	0.4363	0.100*
C13	0.9312 (4)	0.7257 (7)	0.40249 (13)	0.0757 (11)
H13	1.0101	0.6419	0.3972	0.091*
C14	0.7436 (4)	−0.3798 (5)	0.25756 (10)	0.0623 (9)
H14A	0.7213	−0.3417	0.2303	0.093*
H14B	0.6626	−0.4558	0.2666	0.093*
H14C	0.8301	−0.4652	0.2600	0.093*
C15	0.8745 (7)	1.2200 (7)	0.45951 (14)	0.1050 (18)
H15A	0.7848	1.2962	0.4611	0.157*
H15B	0.9449	1.3065	0.4479	0.157*
H15C	0.9127	1.1789	0.4856	0.157*
C16	0.3056 (3)	0.4990 (4)	0.36655 (8)	0.0397 (6)
C17	0.3040 (4)	0.6399 (5)	0.39722 (10)	0.0530 (8)
H17	0.2963	0.7815	0.3917	0.064*
C18	0.3140 (4)	0.5713 (6)	0.43625 (10)	0.0669 (10)
H18	0.3134	0.6685	0.4566	0.080*
C19	0.3247 (4)	0.3641 (6)	0.44559 (11)	0.0619 (9)
C20	0.3257 (5)	0.2259 (6)	0.41467 (12)	0.0685 (10)
H20	0.3332	0.0845	0.4203	0.082*
C21	0.3159 (4)	0.2887 (5)	0.37551 (11)	0.0587 (8)
H21	0.3163	0.1907	0.3553	0.070*
C22	0.3344 (6)	0.2865 (9)	0.48800 (12)	0.0999 (16)
H22A	0.2391	0.2933	0.4978	0.150*
H22B	0.4019	0.3719	0.5041	0.150*
H22C	0.3684	0.1450	0.4889	0.150*
N1	0.7693 (3)	−0.1908 (4)	0.28160 (7)	0.0447 (6)
O1	0.4209 (2)	0.5016 (4)	0.30040 (7)	0.0603 (6)
O2	0.1565 (2)	0.5055 (4)	0.29878 (7)	0.0611 (6)
O3	0.2956 (3)	0.8137 (4)	0.31892 (8)	0.0753 (8)
S1	0.29376 (8)	0.58894 (12)	0.31685 (2)	0.0444 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0485 (16)	0.0467 (17)	0.0488 (16)	−0.0024 (13)	0.0038 (13)	0.0100 (13)
C2	0.0406 (15)	0.070 (2)	0.065 (2)	−0.0036 (15)	0.0044 (14)	0.0021 (18)
C3	0.0442 (16)	0.058 (2)	0.066 (2)	0.0095 (15)	0.0092 (14)	0.0037 (16)
C4	0.0411 (15)	0.0583 (19)	0.0555 (17)	0.0006 (14)	−0.0001 (13)	0.0049 (16)
C5	0.0463 (16)	0.0573 (19)	0.0573 (17)	0.0138 (15)	0.0063 (13)	0.0017 (16)
C6	0.0443 (16)	0.063 (2)	0.067 (2)	−0.0036 (15)	0.0009 (15)	0.0071 (17)
C7	0.0491 (17)	0.0618 (19)	0.0572 (18)	−0.0059 (15)	0.0013 (14)	0.0045 (14)
C8	0.0536 (17)	0.0527 (17)	0.0471 (15)	−0.0037 (14)	0.0054 (13)	0.0111 (12)
C9	0.0517 (19)	0.081 (3)	0.073 (2)	−0.0037 (19)	0.0066 (17)	−0.006 (2)
C10	0.077 (3)	0.083 (3)	0.077 (3)	0.018 (2)	0.017 (2)	−0.007 (2)
C11	0.098 (3)	0.056 (2)	0.0452 (17)	−0.007 (2)	0.0031 (18)	−0.0002 (16)
C12	0.064 (2)	0.094 (3)	0.090 (3)	−0.015 (2)	−0.007 (2)	−0.023 (3)
C13	0.055 (2)	0.077 (3)	0.094 (3)	0.0079 (19)	−0.0004 (19)	−0.020 (2)
C14	0.086 (3)	0.0438 (18)	0.0580 (19)	0.0003 (17)	0.0103 (17)	0.0020 (15)
C15	0.172 (5)	0.071 (3)	0.070 (3)	−0.007 (3)	0.004 (3)	−0.016 (2)
C16	0.0302 (12)	0.0407 (14)	0.0484 (14)	0.0002 (11)	0.0045 (10)	−0.0091 (12)
C17	0.0646 (19)	0.0361 (15)	0.0587 (18)	0.0034 (14)	0.0073 (15)	−0.0088 (14)
C18	0.082 (2)	0.069 (2)	0.0492 (18)	0.005 (2)	0.0062 (17)	−0.0137 (18)
C19	0.063 (2)	0.067 (2)	0.0559 (19)	−0.0052 (17)	0.0040 (16)	0.0039 (17)
C20	0.088 (3)	0.0448 (18)	0.071 (2)	−0.0081 (18)	0.000 (2)	0.0052 (18)
C21	0.075 (2)	0.0398 (17)	0.0613 (19)	−0.0021 (16)	0.0046 (16)	−0.0086 (15)
C22	0.126 (4)	0.109 (4)	0.063 (2)	−0.008 (3)	0.000 (3)	0.017 (3)
N1	0.0504 (13)	0.0415 (13)	0.0426 (12)	0.0024 (11)	0.0059 (10)	0.0067 (11)
O1	0.0446 (12)	0.0814 (17)	0.0565 (13)	0.0081 (11)	0.0131 (10)	−0.0025 (12)
O2	0.0406 (11)	0.0816 (17)	0.0599 (13)	0.0075 (11)	−0.0034 (9)	−0.0081 (12)
O3	0.109 (2)	0.0446 (13)	0.0723 (16)	0.0049 (14)	0.0096 (15)	0.0082 (12)
S1	0.0406 (4)	0.0440 (4)	0.0488 (4)	0.0053 (3)	0.0045 (3)	−0.0026 (3)

Geometric parameters (Å, º) top

C1—C2	1.385 (5)	C14—N1	1.470 (4)
C1—C5	1.393 (4)	C14—H14A	0.9600
C1—C6	1.474 (5)	C14—H14B	0.9600
C2—C3	1.358 (5)	C14—H14C	0.9600
C2—H2	0.9300	C15—H15A	0.9600
C3—N1	1.336 (4)	C15—H15B	0.9600
C3—H3	0.9300	C15—H15C	0.9600
C4—N1	1.346 (4)	C16—C17	1.379 (4)
C4—C5	1.366 (5)	C16—C21	1.386 (4)
C4—H4	0.9300	C16—S1	1.775 (3)
C5—H5	0.9300	C17—C18	1.389 (5)
C6—C7	1.296 (5)	C17—H17	0.9300
C6—H6	0.9300	C18—C19	1.370 (5)
C7—C8	1.474 (5)	C18—H18	0.9300
C7—H7	0.9300	C19—C20	1.374 (5)
C8—C9	1.373 (5)	C19—C22	1.517 (5)
C8—C13	1.378 (5)	C20—C21	1.383 (5)
C9—C10	1.386 (6)	C20—H20	0.9300
C9—H9	0.9300	C21—H21	0.9300
C10—C11	1.357 (6)	C22—H22A	0.9600
C10—H10	0.9300	C22—H22B	0.9600
C11—C12	1.373 (6)	C22—H22C	0.9600
C11—C15	1.507 (6)	O1—S1	1.446 (2)
C12—C13	1.374 (6)	O2—S1	1.449 (2)
C12—H12	0.9300	O3—S1	1.446 (3)
C13—H13	0.9300

C2—C1—C5	116.4 (3)	N1—C14—H14C	109.5
C2—C1—C6	118.6 (3)	H14A—C14—H14C	109.5
C5—C1—C6	124.9 (3)	H14B—C14—H14C	109.5
C3—C2—C1	120.9 (3)	C11—C15—H15A	109.5
C3—C2—H2	119.5	C11—C15—H15B	109.5
C1—C2—H2	119.5	H15A—C15—H15B	109.5
N1—C3—C2	121.5 (3)	C11—C15—H15C	109.5
N1—C3—H3	119.3	H15A—C15—H15C	109.5
C2—C3—H3	119.3	H15B—C15—H15C	109.5
N1—C4—C5	120.7 (3)	C17—C16—C21	118.7 (3)
N1—C4—H4	119.6	C17—C16—S1	119.8 (2)
C5—C4—H4	119.6	C21—C16—S1	121.5 (2)
C4—C5—C1	120.8 (3)	C16—C17—C18	120.3 (3)
C4—C5—H5	119.6	C16—C17—H17	119.9
C1—C5—H5	119.6	C18—C17—H17	119.9
C7—C6—C1	125.9 (3)	C19—C18—C17	121.7 (3)
C7—C6—H6	117.0	C19—C18—H18	119.1
C1—C6—H6	117.0	C17—C18—H18	119.1
C6—C7—C8	126.1 (3)	C18—C19—C20	117.2 (3)
C6—C7—H7	117.0	C18—C19—C22	122.4 (4)
C8—C7—H7	117.0	C20—C19—C22	120.4 (4)
C9—C8—C13	116.0 (3)	C19—C20—C21	122.6 (3)
C9—C8—C7	119.5 (3)	C19—C20—H20	118.7
C13—C8—C7	124.5 (3)	C21—C20—H20	118.7
C8—C9—C10	121.7 (4)	C20—C21—C16	119.5 (3)
C8—C9—H9	119.2	C20—C21—H21	120.3
C10—C9—H9	119.2	C16—C21—H21	120.3
C11—C10—C9	121.7 (4)	C19—C22—H22A	109.5
C11—C10—H10	119.1	C19—C22—H22B	109.5
C9—C10—H10	119.1	H22A—C22—H22B	109.5
C10—C11—C12	117.2 (4)	C19—C22—H22C	109.5
C10—C11—C15	122.0 (4)	H22A—C22—H22C	109.5
C12—C11—C15	120.8 (4)	H22B—C22—H22C	109.5
C11—C12—C13	121.2 (4)	C3—N1—C4	119.6 (3)
C11—C12—H12	119.4	C3—N1—C14	120.5 (3)
C13—C12—H12	119.4	C4—N1—C14	119.8 (3)
C12—C13—C8	122.2 (4)	O1—S1—O3	113.58 (17)
C12—C13—H13	118.9	O1—S1—O2	112.85 (14)
C8—C13—H13	118.9	O3—S1—O2	113.34 (17)
N1—C14—H14A	109.5	O1—S1—C16	104.78 (13)
N1—C14—H14B	109.5	O3—S1—C16	106.24 (15)
H14A—C14—H14B	109.5	O2—S1—C16	105.02 (14)

C5—C1—C2—C3	−0.6 (5)	C21—C16—C17—C18	0.6 (5)
C6—C1—C2—C3	178.0 (3)	S1—C16—C17—C18	−179.7 (3)
C1—C2—C3—N1	0.0 (5)	C16—C17—C18—C19	−0.4 (6)
N1—C4—C5—C1	−0.4 (5)	C17—C18—C19—C20	0.2 (6)
C2—C1—C5—C4	0.8 (5)	C17—C18—C19—C22	−179.5 (4)
C6—C1—C5—C4	−177.7 (3)	C18—C19—C20—C21	−0.2 (6)
C2—C1—C6—C7	−177.8 (3)	C22—C19—C20—C21	179.5 (4)
C5—C1—C6—C7	0.6 (6)	C19—C20—C21—C16	0.4 (6)
C1—C6—C7—C8	178.2 (3)	C17—C16—C21—C20	−0.6 (5)
C6—C7—C8—C9	174.9 (4)	S1—C16—C21—C20	179.6 (3)
C6—C7—C8—C13	−5.5 (6)	C2—C3—N1—C4	0.4 (5)
C13—C8—C9—C10	0.4 (6)	C2—C3—N1—C14	177.8 (3)
C7—C8—C9—C10	180.0 (4)	C5—C4—N1—C3	−0.2 (5)
C8—C9—C10—C11	−0.2 (7)	C5—C4—N1—C14	−177.6 (3)
C9—C10—C11—C12	−0.4 (6)	C17—C16—S1—O1	124.9 (2)
C9—C10—C11—C15	179.7 (4)	C21—C16—S1—O1	−55.3 (3)
C10—C11—C12—C13	0.9 (7)	C17—C16—S1—O3	4.4 (3)
C15—C11—C12—C13	−179.2 (4)	C21—C16—S1—O3	−175.8 (3)
C11—C12—C13—C8	−0.8 (7)	C17—C16—S1—O2	−116.0 (3)
C9—C8—C13—C12	0.1 (6)	C21—C16—S1—O2	63.8 (3)
C7—C8—C13—C12	−179.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2ⁱ	0.93	2.42	3.273 (4)	152
C14—H14B···O1ⁱⁱ	0.96	2.59	3.482 (4)	155

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₆N⁺·C₇H₇O₃S⁻
M_r	381.48
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	9.1380 (6), 6.4257 (5), 33.884 (2)
β (°)	95.004 (4)
V (Å³)	1982.0 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.28 × 0.22 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.950, 0.964
No. of measured, independent and observed [I > 2σ(I)] reflections	18512, 4902, 3850
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.670

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.075, 0.184, 1.13
No. of reflections	4902
No. of parameters	247
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.57, −0.37

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2ⁱ	0.93	2.42	3.273 (4)	152
C14—H14B···O1ⁱⁱ	0.96	2.59	3.482 (4)	155

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

Acknowledgements

The authors wish to acknowledge the SAIF, IIT Madras for the data collection. MK would also like to thank the Council of Scientific and Industrial Research (CSIR), New Delhi, for providing financial support (project No. 03 (1200)/EMR-II).

References

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