1-(4-Methoxy­benz­yl)pyridinium p-toluene­sulfonate

Achilonu, M.C.; Janse van Rensburg, J.M.; Westhuizen, J.H. van der; Roodt, A.

doi:10.1107/S1600536807046703

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1-(4-Methoxybenzyl)pyridinium p-toluenesulfonate

M. C. Achilonu, J. M. Janse van Rensburg, J. H. van der Westhuizen and A. Roodt

In the title compound, C₁₃H₁₄NO⁺·C₇H₇O₃S⁻, intermolecular C—H

O hydrogen bonds in the range 3.26–3.45 Å are observed. The p-toluenesulfonate anions stack in a tail-to-tail (i.e. methyl-to-methyl) fashion, with an interplanar toluene–toluene distance of 3.472 Å.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807046703/ez2098sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807046703/ez2098Isup2.hkl Contains datablock I

CCDC reference: 667362

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Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R factor = 0.036
wR factor = 0.092
Data-to-parameter ratio = 18.8

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PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT153_ALERT_1_C The su's on the Cell Axes   are Equal (x 100000)        500 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
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Comment top

Tosylation of p-methoxybenzylalcohol with tosylchloride in dry pyridine yielded N-(4-methoxybenzyl)-pyridinium toluene-4-sulfonate, (I), as a crystalline product in almost quantitative yield. This product exhibited not only NMR signals corresponding to the initially anticipated benzylic tosylate, but also peaks from a pyridine moiety, in a 1:1 ratio. Electro spray mass spectrometry showed a m/e = 200 base peak in positive mode corresponding to a N-(4-methoxybenzyl)-pyridinium cation and a m/e 171 base peak in negative mode corresponding to a toluene-4-sulfonic acid anion. The unexpected nature of this product and the reaction responsible for it prompted us to prove its structure unequivocally with crystallography. Benzylpyridinium derivatives are described as structurally and magnetically 1-D molecular solids. This is in part due to the cation being nonplanar. The stacking structure of benzylpyridinium molecules can be fine-tuned by varying substituents on the aromatic rings, creating a more conductive solid (Ren et al., 2002).

The title compound, (I), crystallizes with anionic [p-Ts]^- (p-Ts = p-toluenesulfonate) and cationic moieties [MeOBzPy]⁺ (MeOBzPy = 4-methoxy-benzylpyridinium) respectively. In the [MeOBzPy]⁺ cation packing of the pyridinium and 4-methoxybenzyl rings induces a slight distortion from ideal tetrahedral geometry at C1 (C21—C1—N angle of 111.25 (3)°). The methoxy moiety itself is almost in plane with the benzene ring as shown by the torsion angle of 178.23 (3)° through atoms C25—C24—O4—C27. In comparing the rotation of the pyridinium and 4-methoxyphenyl ring systems with respect to the plane formed by atoms C21–C1–N, dihedral angles of 77.6 (1)° and 73.7 (1)°, respectively, are observed. Other bond distances and angles for (I) fall well within the range of similar compounds reported to date [Cambridge Structural Database (CSD), Version 5.27, August 2006 update; Allen, 2002]. In this structure no significant π–π stacking is observed between the [MeOBzPy]⁺ moieties, as typically found in other similar compounds (Ren et al., 2002).

In the crystal packing, C1 of the [MeOBzPy]⁺ molecule acts as a hydrogen-bond donor, via H1B, to the sulfonate atom O1. Likewise, C32 acts as a donor, via H32, to atom O3, resulting in a intermolecular link and the preferred conformation of the sulfonate O-atoms (Fig. 1). The p-toluenesulfonate anions stack in a "tail to tail" fashion with an interplanar toluene–phenyl distance of 3.472 Å (Fig. 2).

Related literature top

For similar benzylpyridinium compounds, see: Ren et al., 2002. For reference bond-length data, see: Allen (2002).

Experimental top

p-Toluenesulfonyl chloride (3.0 g, 15.7 mmol) and 4-methoxybenzyl alcohol (2.0 g, 14.7 mmol) were dissolved in dry pyridine (3.5 ml). The reaction was left for 5 days at room temperature with a CaCl₂ tube fitted for protection against atmospheric moisture. The resulting solidified reaction mixture was washed with hexane. Recrystallization of the product from dichloromethane yielded 1-(4-methoxybenzyl)-pyridinium p-toluene-4-sulfonate (4.91 g, 90%) as colourless cuboid crystals; mp 128–131°; δ_H (300 MHz; CDCl₃; Me₄Si) 9.30 (2H, dd, J = 1.0 Hz and 8.0 Hz, H-36, H-32); 8.73 (2H, t, J = 8.0 Hz, H-35, H-33); 8.22 (1H, t, J = 8.0 Hz, H-34); 7.50 (2H, d, J = 9.0 Hz, H-25, H-23); 6.75 (2H, d, J = 9.0 Hz, H-26, H-22); 7.10 (2H, d, J = 8.0 Hz, H-15, H-13); 7.77 (2H, d, J = 8.0 Hz, H-16, H-12); 5.91 (2H, s, –CH₂–, H-1); 3.74 (3H, s, Ar-OCH₃, H-27); 2.34 (3H, s, Ar—CH₃, H-17); δ¹³_C{H} (75 MHz; CDCl₃) 160.9 (C-24), 145.4 (C-32 and C-36), 144.2 (C-34), 142.6 (C-11'), 139.8 (C-14), 131.6(C-22 and C-26), 129.2 (C-13 and C-15), 128.6 (C-33 and C-35), 126.3 (C-12 and C-16), 125.7 (C-21), 115.1 (C-23 and C-25), 64.5 (–CH₂–, C-1), 55.7 (Ar-OCH₃, C-27), and 21.7 (Ar—CH₃, C-17); m/z: (positive mode) 201.3 ([M+1]⁺, 10%), 200.3 (M⁺, 60%), 122.2 (24%), 121.2(100%); m/z (negative mode) 172.2 ([(M-1]^-, 8%), 171.2 (M⁺, 100%).

Structure description top

For similar benzylpyridinium compounds, see: Ren et al., 2002. For reference bond-length data, see: Allen (2002).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus (Bruker, 2004) and XPREP (Bruker, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. A view of (I) showing the atom-numbering scheme with displacement ellipsoids at the 30% probability level.
	Fig. 2. Partly occupied unit-cell indicating the packing fashion. Symmetry operators for molecules 1 and 2: 1) 1 - x, 1 - y, 2 - z. 2) x, y, z.

1-(4-Methoxybenzyl)pyridinium p-toluenesulfonate top

Crystal data top

C₁₃H₁₄NO⁺·C₇H₇O₃S⁻	F(000) = 784
M_r = 371.44	D_x = 1.377 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2yn	Cell parameters from 9909 reflections
a = 9.668 (5) Å	θ = 2.4–28.3°
b = 20.096 (5) Å	µ = 0.21 mm⁻¹
c = 9.852 (5) Å	T = 100 K
β = 110.639 (5)°	Cuboid, colourless
V = 1791.3 (14) Å³	0.4 × 0.2 × 0.1 mm
Z = 4

Data collection top

Bruker X8 APEXII 4K KappaCCD diffractometer	4447 independent reflections
Radiation source: fine-focus sealed tube	3789 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
ω and φ scans	θ_max = 28.3°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −12→12
T_min = 0.922, T_max = 0.979	k = −25→26
32879 measured reflections	l = −13→13

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.036	w = 1/[σ²(F_o²) + (0.0394P)² + 0.9825P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.092	(Δ/σ)_max = 0.002
S = 1.06	Δρ_max = 0.32 e Å⁻³
4447 reflections	Δρ_min = −0.59 e Å⁻³
237 parameters

Crystal data top

C₁₃H₁₄NO⁺·C₇H₇O₃S⁻	V = 1791.3 (14) Å³
M_r = 371.44	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.668 (5) Å	µ = 0.21 mm⁻¹
b = 20.096 (5) Å	T = 100 K
c = 9.852 (5) Å	0.4 × 0.2 × 0.1 mm
β = 110.639 (5)°

Data collection top

Bruker X8 APEXII 4K KappaCCD diffractometer	4447 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	3789 reflections with I > 2σ(I)
T_min = 0.922, T_max = 0.979	R_int = 0.043
32879 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.092	H-atom parameters constrained
S = 1.06	Δρ_max = 0.32 e Å⁻³
4447 reflections	Δρ_min = −0.59 e Å⁻³
237 parameters

Special details top

Experimental. The intensity data was collected on a Bruker X8 Apex II 4 K Kappa CCD diffractometer using an exposure time of 20 s/frame. A total of 1896 frames were collected with a frame width of 0.5° covering up to θ = 28.3° with 100° completeness accomplished.

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.

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

	x	y	z	U_iso*/U_eq
C1	0.60595 (14)	0.59526 (7)	0.48918 (14)	0.0132 (3)
H1A	0.6495	0.5553	0.4661	0.016*
H1B	0.5078	0.5841	0.4876	0.016*
C11	0.24154 (13)	0.57692 (7)	0.70133 (14)	0.0109 (3)
C12	0.33487 (14)	0.61530 (7)	0.81413 (15)	0.0127 (3)
H12	0.3693	0.6561	0.7947	0.015*
C13	0.37633 (14)	0.59236 (7)	0.95594 (15)	0.0137 (3)
H13	0.4392	0.6181	1.0308	0.016*
C14	0.32567 (14)	0.53154 (7)	0.98852 (14)	0.0131 (3)
C15	0.23085 (14)	0.49412 (7)	0.87397 (15)	0.0138 (3)
H15	0.1953	0.4536	0.8934	0.017*
C16	0.18852 (14)	0.51633 (7)	0.73120 (14)	0.0127 (3)
H16	0.1252	0.4908	0.6562	0.015*
C17	0.37284 (15)	0.50757 (8)	1.14311 (15)	0.0174 (3)
H17A	0.4769	0.515	1.1905	0.026*
H17B	0.3522	0.4609	1.1442	0.026*
H17C	0.3194	0.5315	1.1932	0.026*
C21	0.69908 (14)	0.61896 (7)	0.63891 (14)	0.0116 (3)
C22	0.83990 (14)	0.59323 (7)	0.70717 (14)	0.0131 (3)
H22	0.8782	0.5631	0.658	0.016*
C23	0.92469 (14)	0.61195 (7)	0.84837 (15)	0.0134 (3)
H23	1.0187	0.5943	0.8935	0.016*
C24	0.86712 (14)	0.65725 (7)	0.92094 (14)	0.0118 (3)
C25	0.72601 (14)	0.68448 (7)	0.85261 (14)	0.0129 (3)
H25	0.6884	0.7153	0.901	0.015*
C26	0.64303 (14)	0.66515 (7)	0.71257 (14)	0.0123 (3)
H26	0.5493	0.683	0.6671	0.015*
C27	1.08315 (15)	0.65152 (8)	1.13428 (15)	0.0194 (3)
H27A	1.0742	0.6042	1.1423	0.029*
H27B	1.1233	0.6707	1.2295	0.029*
H27C	1.1476	0.6609	1.0816	0.029*
C32	0.47083 (14)	0.68464 (7)	0.32476 (14)	0.0122 (3)
H32	0.393	0.6777	0.3579	0.015*
C33	0.45966 (15)	0.73291 (7)	0.22225 (14)	0.0145 (3)
H33	0.374	0.7582	0.1853	0.017*
C34	0.57662 (15)	0.74365 (7)	0.17419 (15)	0.0164 (3)
H34	0.5701	0.776	0.1048	0.02*
C35	0.70346 (15)	0.70537 (8)	0.23123 (15)	0.0174 (3)
H35	0.7832	0.7121	0.2009	0.021*
C36	0.71029 (14)	0.65740 (7)	0.33293 (15)	0.0148 (3)
H36	0.7951	0.6316	0.3715	0.018*
N	0.59458 (11)	0.64748 (6)	0.37720 (12)	0.0108 (2)
O1	0.24697 (11)	0.55275 (5)	0.44539 (11)	0.0182 (2)
O2	0.03159 (10)	0.60938 (5)	0.46323 (11)	0.0174 (2)
O3	0.26504 (10)	0.66785 (5)	0.52365 (10)	0.0145 (2)
O4	0.94071 (10)	0.67943 (5)	1.05911 (10)	0.0161 (2)
S	0.19217 (3)	0.603727 (16)	0.51832 (3)	0.01009 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0142 (6)	0.0113 (7)	0.0119 (6)	−0.0007 (5)	0.0018 (5)	0.0025 (5)
C11	0.0092 (5)	0.0124 (7)	0.0117 (6)	0.0022 (5)	0.0042 (5)	0.0011 (5)
C12	0.0128 (6)	0.0109 (6)	0.0151 (6)	−0.0008 (5)	0.0057 (5)	0.0000 (5)
C13	0.0135 (6)	0.0150 (7)	0.0121 (6)	−0.0011 (5)	0.0039 (5)	−0.0025 (5)
C14	0.0132 (6)	0.0144 (7)	0.0130 (6)	0.0035 (5)	0.0063 (5)	0.0020 (5)
C15	0.0141 (6)	0.0111 (7)	0.0176 (7)	−0.0003 (5)	0.0073 (5)	0.0019 (5)
C16	0.0112 (5)	0.0123 (7)	0.0140 (6)	−0.0004 (5)	0.0037 (5)	−0.0015 (5)
C17	0.0198 (6)	0.0185 (7)	0.0146 (7)	0.0014 (6)	0.0070 (5)	0.0028 (6)
C21	0.0122 (6)	0.0113 (6)	0.0103 (6)	−0.0018 (5)	0.0028 (5)	0.0020 (5)
C22	0.0138 (6)	0.0124 (7)	0.0130 (6)	0.0015 (5)	0.0045 (5)	−0.0004 (5)
C23	0.0107 (5)	0.0150 (7)	0.0130 (6)	0.0028 (5)	0.0023 (5)	0.0018 (5)
C24	0.0121 (6)	0.0136 (7)	0.0095 (6)	−0.0009 (5)	0.0035 (5)	0.0014 (5)
C25	0.0138 (6)	0.0137 (7)	0.0129 (6)	0.0013 (5)	0.0068 (5)	0.0007 (5)
C26	0.0098 (5)	0.0134 (7)	0.0131 (6)	0.0006 (5)	0.0034 (5)	0.0028 (5)
C27	0.0139 (6)	0.0265 (8)	0.0138 (7)	0.0028 (6)	−0.0001 (5)	−0.0015 (6)
C32	0.0101 (5)	0.0151 (7)	0.0118 (6)	0.0006 (5)	0.0045 (5)	−0.0021 (5)
C33	0.0161 (6)	0.0126 (7)	0.0139 (6)	0.0032 (5)	0.0042 (5)	−0.0007 (5)
C34	0.0234 (7)	0.0127 (7)	0.0141 (6)	−0.0045 (5)	0.0077 (5)	−0.0011 (5)
C35	0.0152 (6)	0.0224 (8)	0.0175 (7)	−0.0060 (5)	0.0092 (5)	−0.0049 (6)
C36	0.0092 (5)	0.0181 (7)	0.0165 (7)	−0.0001 (5)	0.0039 (5)	−0.0038 (5)
N	0.0105 (5)	0.0115 (6)	0.0097 (5)	−0.0004 (4)	0.0027 (4)	−0.0014 (4)
O1	0.0246 (5)	0.0158 (5)	0.0153 (5)	0.0057 (4)	0.0084 (4)	−0.0011 (4)
O2	0.0093 (4)	0.0252 (6)	0.0158 (5)	0.0009 (4)	0.0019 (4)	0.0039 (4)
O3	0.0160 (4)	0.0141 (5)	0.0137 (5)	−0.0020 (4)	0.0055 (4)	0.0016 (4)
O4	0.0137 (4)	0.0223 (6)	0.0099 (5)	0.0032 (4)	0.0011 (4)	−0.0027 (4)
S	0.00905 (14)	0.01113 (17)	0.00985 (15)	0.00089 (11)	0.00302 (11)	0.00019 (12)

Geometric parameters (Å, º) top

C1—N	1.4983 (17)	C23—H23	0.93
C1—C21	1.5091 (19)	C24—O4	1.3693 (17)
C1—H1A	0.97	C24—C25	1.4022 (18)
C1—H1B	0.97	C25—C26	1.3849 (19)
C11—C12	1.3918 (19)	C25—H25	0.93
C11—C16	1.3921 (19)	C26—H26	0.93
C11—S	1.7783 (16)	C27—O4	1.4285 (17)
C12—C13	1.389 (2)	C27—H27A	0.96
C12—H12	0.93	C27—H27B	0.96
C13—C14	1.3954 (19)	C27—H27C	0.96
C13—H13	0.93	C32—N	1.3492 (17)
C14—C15	1.397 (2)	C32—C33	1.377 (2)
C14—C17	1.507 (2)	C32—H32	0.93
C15—C16	1.393 (2)	C33—C34	1.3881 (19)
C15—H15	0.93	C33—H33	0.93
C16—H16	0.93	C34—C35	1.388 (2)
C17—H17A	0.96	C34—H34	0.93
C17—H17B	0.96	C35—C36	1.375 (2)
C17—H17C	0.96	C35—H35	0.93
C21—C22	1.3884 (19)	C36—N	1.3511 (17)
C21—C26	1.3996 (19)	C36—H36	0.93
C22—C23	1.3945 (19)	O1—S	1.4542 (11)
C22—H22	0.93	O2—S	1.4573 (12)
C23—C24	1.3895 (19)	O3—S	1.4606 (11)

N—C1—C21	111.25 (11)	O4—C24—C25	115.27 (12)
N—C1—H1A	109.4	C23—C24—C25	120.47 (12)
C21—C1—H1A	109.4	C26—C25—C24	119.52 (12)
N—C1—H1B	109.4	C26—C25—H25	120.2
C21—C1—H1B	109.4	C24—C25—H25	120.2
H1A—C1—H1B	108	C25—C26—C21	120.55 (12)
C12—C11—C16	119.96 (12)	C25—C26—H26	119.7
C12—C11—S	120.55 (11)	C21—C26—H26	119.7
C16—C11—S	119.48 (10)	O4—C27—H27A	109.5
C13—C12—C11	119.67 (13)	O4—C27—H27B	109.5
C13—C12—H12	120.2	H27A—C27—H27B	109.5
C11—C12—H12	120.2	O4—C27—H27C	109.5
C12—C13—C14	121.44 (13)	H27A—C27—H27C	109.5
C12—C13—H13	119.3	H27B—C27—H27C	109.5
C14—C13—H13	119.3	N—C32—C33	120.03 (12)
C13—C14—C15	118.00 (12)	N—C32—H32	120
C13—C14—C17	120.45 (12)	C33—C32—H32	120
C15—C14—C17	121.55 (13)	C32—C33—C34	119.81 (13)
C16—C15—C14	121.27 (13)	C32—C33—H33	120.1
C16—C15—H15	119.4	C34—C33—H33	120.1
C14—C15—H15	119.4	C35—C34—C33	119.04 (13)
C11—C16—C15	119.66 (12)	C35—C34—H34	120.5
C11—C16—H16	120.2	C33—C34—H34	120.5
C15—C16—H16	120.2	C36—C35—C34	119.49 (13)
C14—C17—H17A	109.5	C36—C35—H35	120.3
C14—C17—H17B	109.5	C34—C35—H35	120.3
H17A—C17—H17B	109.5	N—C36—C35	120.41 (13)
C14—C17—H17C	109.5	N—C36—H36	119.8
H17A—C17—H17C	109.5	C35—C36—H36	119.8
H17B—C17—H17C	109.5	C32—N—C36	121.20 (12)
C22—C21—C26	119.25 (12)	C32—N—C1	119.65 (11)
C22—C21—C1	120.08 (12)	C36—N—C1	119.13 (11)
C26—C21—C1	120.63 (12)	C24—O4—C27	117.11 (11)
C21—C22—C23	120.93 (13)	O1—S—O2	113.37 (6)
C21—C22—H22	119.5	O1—S—O3	112.59 (6)
C23—C22—H22	119.5	O2—S—O3	112.43 (6)
C24—C23—C22	119.26 (12)	O1—S—C11	105.86 (7)
C24—C23—H23	120.4	O2—S—C11	105.74 (6)
C22—C23—H23	120.4	O3—S—C11	106.09 (6)
O4—C24—C23	124.25 (12)

C16—C11—C12—C13	0.95 (19)	C22—C21—C26—C25	−0.8 (2)
S—C11—C12—C13	−177.72 (10)	C1—C21—C26—C25	176.94 (12)
C11—C12—C13—C14	−0.4 (2)	N—C32—C33—C34	−0.7 (2)
C12—C13—C14—C15	−0.28 (19)	C32—C33—C34—C35	−0.2 (2)
C12—C13—C14—C17	179.68 (12)	C33—C34—C35—C36	0.5 (2)
C13—C14—C15—C16	0.43 (19)	C34—C35—C36—N	0.0 (2)
C17—C14—C15—C16	−179.53 (12)	C33—C32—N—C36	1.2 (2)
C12—C11—C16—C15	−0.80 (19)	C33—C32—N—C1	179.75 (12)
S—C11—C16—C15	177.88 (10)	C35—C36—N—C32	−0.9 (2)
C14—C15—C16—C11	0.11 (19)	C35—C36—N—C1	−179.44 (12)
N—C1—C21—C22	−107.37 (14)	C21—C1—N—C32	−101.63 (14)
N—C1—C21—C26	74.91 (15)	C21—C1—N—C36	76.93 (15)
C26—C21—C22—C23	1.1 (2)	C23—C24—O4—C27	−2.85 (19)
C1—C21—C22—C23	−176.69 (12)	C25—C24—O4—C27	178.23 (12)
C21—C22—C23—C24	−0.3 (2)	C12—C11—S—O1	118.83 (11)
C22—C23—C24—O4	−179.58 (12)	C16—C11—S—O1	−59.85 (12)
C22—C23—C24—C25	−0.7 (2)	C12—C11—S—O2	−120.61 (11)
O4—C24—C25—C26	179.93 (12)	C16—C11—S—O2	60.72 (12)
C23—C24—C25—C26	1.0 (2)	C12—C11—S—O3	−1.01 (12)
C24—C25—C26—C21	−0.2 (2)	C16—C11—S—O3	−179.68 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···O1	0.97	2.49	3.450 (2)	172
C32—H32···O3	0.93	2.38	3.265 (2)	159

Experimental details

Crystal data
Chemical formula	C₁₃H₁₄NO⁺·C₇H₇O₃S⁻
M_r	371.44
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	9.668 (5), 20.096 (5), 9.852 (5)
β (°)	110.639 (5)
V (Å³)	1791.3 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.4 × 0.2 × 0.1

Data collection
Diffractometer	Bruker X8 APEXII 4K KappaCCD
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.922, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	32879, 4447, 3789
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.092, 1.06
No. of reflections	4447
No. of parameters	237
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.59

Computer programs: APEX2 (Bruker, 2005), SAINT-Plus (Bruker, 2004) and XPREP (Bruker, 2004), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), DIAMOND (Brandenburg & Putz, 2005), WinGX (Farrugia, 1999).

Selected bond angles (º) top

N—C1—C21

111.25 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···O1	0.97	2.49	3.450 (2)	171.7
C32—H32···O3	0.93	2.38	3.265 (2)	159

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