1-(Phthalimidometh-yl)pyridinium p-toluene-sulfonate.

In the crystal of the title compound, C(14)H(11)N(2)O(2) (+)·C(7)H(7)O(3)S(-), the cation and anion inter-act by way of an aromatic π-π inter-action [centroid-centroid separation = 3.5783 (2) Å] and a T-stacking (C-H⋯π) inter-action between cations. The dihedral angle between the aromatic rings in the cation is 61.73 (8)°. The ionic units are aligned in a zigzag fashion in the b-axis direction.

Related literature

For medicinal background, see: Al-Madhoun et al. (2002 ▶); Arner & Eriksson (1995 ▶); Bello (1974 ▶); Celen et al. (2007 ▶); Eriksson et al. (2002 ▶); Wei et al. (2005 ▶); Welin et al. (2004 ▶).

Experimental

Crystal data

C14H11N2O2 +·C7H7O3S−

M = 410.43

Monoclinic,

a = 7.6944 (5) Å

b = 33.626 (2) Å

c = 7.9426 (5) Å

β = 116.416 (1)°

V = 1840.5 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 90 (2) K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008 ▶) T min = 0.939, T max = 0.958

19080 measured reflections

4482 independent reflections

3753 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.124

S = 1.12

4482 reflections

263 parameters

H-atom parameters constrained

Δρmax = 0.61 e Å−3

Δρmin = −0.38 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz (1999 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808038816/hb2840sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038816/hb2840Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C14H11N2O2+·C7H7O3S−	F(000) = 856
Mr = 410.43	Dx = 1.481 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3297 reflections
a = 7.6944 (5) Å	θ = 2.4–26.4°
b = 33.626 (2) Å	µ = 0.21 mm−1
c = 7.9426 (5) Å	T = 90 K
β = 116.416 (1)°	Block, colourless
V = 1840.5 (2) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Bruker APEX CCD diffractometer	4482 independent reflections
Radiation source: fine-focus sealed tube	3753 reflections with I > 2σ(I)
graphite	Rint = 0.049
Detector resolution: 512 pixels mm-1	θmax = 28.1°, θmin = 2.4°
ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	k = −42→44
Tmin = 0.939, Tmax = 0.958	l = −10→10
19080 measured reflections

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.0508P)2 + 1.1529P] where P = (Fo2 + 2Fc2)/3
4482 reflections	(Δ/σ)max < 0.001
263 parameters	Δρmax = 0.61 e Å−3
0 restraints	Δρmin = −0.38 e Å−3

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.

	x	y	z	Uiso*/Ueq
S1	0.71561 (7)	0.151380 (15)	0.83629 (7)	0.01495 (13)
O1	1.0063 (2)	0.07297 (5)	0.3896 (2)	0.0232 (3)
O2	0.4402 (2)	0.01341 (5)	0.3092 (2)	0.0247 (4)
O3	0.8408 (2)	0.15516 (5)	0.7439 (2)	0.0209 (3)
O4	0.6566 (2)	0.11048 (4)	0.8427 (2)	0.0232 (3)
O5	0.7929 (2)	0.17090 (5)	1.0188 (2)	0.0217 (3)
N1	0.7117 (2)	0.05127 (5)	0.3668 (2)	0.0173 (4)
N2	0.5370 (2)	0.11140 (5)	0.3597 (2)	0.0158 (4)
C1	0.8823 (3)	0.04795 (6)	0.3432 (3)	0.0169 (4)
C2	0.8696 (3)	0.00828 (6)	0.2554 (3)	0.0159 (4)
C3	0.9997 (3)	−0.01049 (6)	0.2060 (3)	0.0191 (4)
H3	1.1166	0.0020	0.2219	0.023*
C4	0.9513 (3)	−0.04884 (7)	0.1314 (3)	0.0228 (5)
H4	1.0367	−0.0628	0.0952	0.027*
C5	0.7805 (3)	−0.06681 (7)	0.1096 (3)	0.0239 (5)
H5	0.7523	−0.0930	0.0598	0.029*
C6	0.6488 (3)	−0.04768 (7)	0.1584 (3)	0.0217 (4)
H6	0.5315	−0.0601	0.1423	0.026*
C7	0.6972 (3)	−0.00982 (6)	0.2314 (3)	0.0170 (4)
C8	0.5931 (3)	0.01743 (6)	0.3028 (3)	0.0179 (4)
C9	0.6823 (3)	0.08173 (6)	0.4785 (3)	0.0204 (4)
H9A	0.8071	0.0953	0.5547	0.025*
H9B	0.6379	0.0694	0.5657	0.025*
C10	0.3571 (3)	0.11045 (6)	0.3473 (3)	0.0177 (4)
H10	0.3245	0.0910	0.4150	0.021*
C11	0.2198 (3)	0.13761 (6)	0.2367 (3)	0.0182 (4)
H11	0.0917	0.1367	0.2257	0.022*
C12	0.2708 (3)	0.16635 (6)	0.1417 (3)	0.0193 (4)
H12	0.1781	0.1855	0.0657	0.023*
C13	0.4584 (3)	0.16703 (6)	0.1581 (3)	0.0192 (4)
H13	0.4952	0.1867	0.0942	0.023*
C14	0.5902 (3)	0.13900 (6)	0.2678 (3)	0.0185 (4)
H14	0.7184	0.1390	0.2790	0.022*
C15	0.4978 (3)	0.17744 (6)	0.6922 (3)	0.0147 (4)
C16	0.3230 (3)	0.16559 (6)	0.6887 (3)	0.0170 (4)
H16	0.3196	0.1430	0.7591	0.020*
C17	0.1535 (3)	0.18648 (6)	0.5831 (3)	0.0180 (4)
H17	0.0355	0.1783	0.5832	0.022*
C18	0.1543 (3)	0.21947 (6)	0.4764 (3)	0.0169 (4)
C19	−0.0316 (3)	0.24117 (7)	0.3577 (3)	0.0221 (5)
H19A	−0.0026	0.2652	0.3049	0.033*
H19B	−0.0957	0.2486	0.4357	0.033*
H19C	−0.1176	0.2238	0.2553	0.033*
C20	0.3304 (3)	0.23071 (6)	0.4797 (3)	0.0184 (4)
H20	0.3336	0.2529	0.4069	0.022*
C21	0.5012 (3)	0.21025 (6)	0.5872 (3)	0.0167 (4)
H21	0.6198	0.2186	0.5889	0.020*

	U11	U22	U33	U12	U13	U23
S1	0.0132 (2)	0.0163 (2)	0.0136 (2)	−0.00043 (18)	0.00446 (18)	−0.00117 (18)
O1	0.0220 (8)	0.0201 (8)	0.0253 (8)	−0.0060 (6)	0.0086 (7)	−0.0012 (6)
O2	0.0170 (7)	0.0361 (9)	0.0229 (8)	−0.0006 (7)	0.0105 (6)	0.0016 (7)
O3	0.0184 (7)	0.0250 (8)	0.0212 (8)	0.0008 (6)	0.0106 (6)	−0.0010 (6)
O4	0.0203 (8)	0.0182 (8)	0.0288 (8)	−0.0001 (6)	0.0087 (7)	0.0030 (6)
O5	0.0183 (7)	0.0290 (8)	0.0130 (7)	0.0020 (6)	0.0027 (6)	−0.0037 (6)
N1	0.0168 (8)	0.0177 (9)	0.0160 (8)	0.0022 (7)	0.0060 (7)	0.0003 (7)
N2	0.0154 (8)	0.0182 (8)	0.0110 (8)	0.0043 (7)	0.0035 (7)	−0.0007 (6)
C1	0.0165 (10)	0.0187 (10)	0.0135 (9)	0.0029 (8)	0.0049 (8)	0.0032 (7)
C2	0.0181 (10)	0.0150 (9)	0.0120 (9)	0.0015 (8)	0.0044 (8)	0.0032 (7)
C3	0.0207 (10)	0.0221 (11)	0.0144 (10)	0.0022 (8)	0.0077 (8)	0.0034 (8)
C4	0.0315 (12)	0.0237 (11)	0.0137 (10)	0.0088 (9)	0.0105 (9)	0.0037 (8)
C5	0.0371 (13)	0.0169 (10)	0.0133 (10)	−0.0018 (9)	0.0074 (9)	0.0002 (8)
C6	0.0262 (11)	0.0208 (11)	0.0149 (10)	−0.0056 (9)	0.0063 (9)	0.0012 (8)
C7	0.0158 (9)	0.0192 (10)	0.0132 (9)	0.0000 (8)	0.0041 (8)	0.0036 (7)
C8	0.0167 (10)	0.0220 (10)	0.0119 (9)	0.0004 (8)	0.0036 (8)	0.0047 (8)
C9	0.0212 (10)	0.0241 (11)	0.0129 (9)	0.0076 (8)	0.0047 (8)	0.0020 (8)
C10	0.0193 (10)	0.0194 (10)	0.0144 (9)	−0.0002 (8)	0.0076 (8)	−0.0026 (8)
C11	0.0148 (9)	0.0223 (10)	0.0149 (10)	0.0009 (8)	0.0044 (8)	−0.0050 (8)
C12	0.0198 (10)	0.0186 (10)	0.0142 (10)	0.0044 (8)	0.0026 (8)	−0.0026 (8)
C13	0.0247 (11)	0.0171 (10)	0.0152 (10)	0.0006 (8)	0.0083 (8)	0.0006 (8)
C14	0.0177 (10)	0.0207 (10)	0.0163 (10)	−0.0010 (8)	0.0068 (8)	−0.0031 (8)
C15	0.0139 (9)	0.0166 (9)	0.0102 (9)	0.0000 (7)	0.0022 (7)	−0.0026 (7)
C16	0.0199 (10)	0.0185 (10)	0.0123 (9)	−0.0001 (8)	0.0068 (8)	0.0001 (7)
C17	0.0163 (9)	0.0213 (10)	0.0158 (10)	0.0002 (8)	0.0067 (8)	−0.0027 (8)
C18	0.0205 (10)	0.0159 (9)	0.0107 (9)	0.0013 (8)	0.0038 (8)	−0.0042 (7)
C19	0.0207 (11)	0.0228 (11)	0.0184 (10)	0.0049 (8)	0.0047 (9)	−0.0019 (8)
C20	0.0233 (10)	0.0155 (10)	0.0139 (9)	−0.0002 (8)	0.0061 (8)	−0.0010 (7)
C21	0.0162 (9)	0.0188 (10)	0.0134 (9)	−0.0037 (8)	0.0050 (8)	−0.0035 (7)

S1—O3	1.4531 (15)	C9—H9B	0.9900
S1—O5	1.4556 (15)	C10—C11	1.377 (3)
S1—O4	1.4562 (16)	C10—H10	0.9500
S1—C15	1.783 (2)	C11—C12	1.386 (3)
O1—C1	1.201 (3)	C11—H11	0.9500
O2—C8	1.208 (2)	C12—C13	1.391 (3)
N1—C8	1.405 (3)	C12—H12	0.9500
N1—C1	1.410 (3)	C13—C14	1.375 (3)
N1—C9	1.437 (3)	C13—H13	0.9500
N2—C10	1.343 (3)	C14—H14	0.9500
N2—C14	1.352 (3)	C15—C21	1.390 (3)
N2—C9	1.482 (3)	C15—C16	1.391 (3)
C1—C2	1.488 (3)	C16—C17	1.387 (3)
C2—C3	1.380 (3)	C16—H16	0.9500
C2—C7	1.393 (3)	C17—C18	1.397 (3)
C3—C4	1.399 (3)	C17—H17	0.9500
C3—H3	0.9500	C18—C20	1.396 (3)
C4—C5	1.386 (3)	C18—C19	1.506 (3)
C4—H4	0.9500	C19—H19A	0.9800
C5—C6	1.393 (3)	C19—H19B	0.9800
C5—H5	0.9500	C19—H19C	0.9800
C6—C7	1.380 (3)	C20—C21	1.390 (3)
C6—H6	0.9500	C20—H20	0.9500
C7—C8	1.486 (3)	C21—H21	0.9500
C9—H9A	0.9900
O3—S1—O5	113.25 (9)	H9A—C9—H9B	108.0
O3—S1—O4	112.78 (9)	N2—C10—C11	120.30 (19)
O5—S1—O4	112.75 (10)	N2—C10—H10	119.8
O3—S1—C15	106.13 (9)	C11—C10—H10	119.8
O5—S1—C15	105.58 (9)	C10—C11—C12	119.12 (19)
O4—S1—C15	105.53 (9)	C10—C11—H11	120.4
C8—N1—C1	112.38 (17)	C12—C11—H11	120.4
C8—N1—C9	123.06 (18)	C11—C12—C13	119.60 (19)
C1—N1—C9	123.35 (18)	C11—C12—H12	120.2
C10—N2—C14	121.75 (18)	C13—C12—H12	120.2
C10—N2—C9	119.46 (18)	C14—C13—C12	119.4 (2)
C14—N2—C9	118.78 (17)	C14—C13—H13	120.3
O1—C1—N1	124.31 (19)	C12—C13—H13	120.3
O1—C1—C2	130.5 (2)	N2—C14—C13	119.82 (19)
N1—C1—C2	105.22 (17)	N2—C14—H14	120.1
C3—C2—C7	121.9 (2)	C13—C14—H14	120.1
C3—C2—C1	129.71 (19)	C21—C15—C16	119.42 (18)
C7—C2—C1	108.40 (18)	C21—C15—S1	120.78 (15)
C2—C3—C4	116.9 (2)	C16—C15—S1	119.78 (15)
C2—C3—H3	121.6	C17—C16—C15	120.50 (19)
C4—C3—H3	121.6	C17—C16—H16	119.8
C5—C4—C3	120.9 (2)	C15—C16—H16	119.8
C5—C4—H4	119.5	C16—C17—C18	120.81 (19)
C3—C4—H4	119.5	C16—C17—H17	119.6
C4—C5—C6	122.1 (2)	C18—C17—H17	119.6
C4—C5—H5	119.0	C20—C18—C17	118.02 (19)
C6—C5—H5	119.0	C20—C18—C19	121.63 (19)
C7—C6—C5	116.7 (2)	C17—C18—C19	120.33 (19)
C7—C6—H6	121.7	C18—C19—H19A	109.5
C5—C6—H6	121.7	C18—C19—H19B	109.5
C6—C7—C2	121.6 (2)	H19A—C19—H19B	109.5
C6—C7—C8	129.7 (2)	C18—C19—H19C	109.5
C2—C7—C8	108.70 (18)	H19A—C19—H19C	109.5
O2—C8—N1	124.3 (2)	H19B—C19—H19C	109.5
O2—C8—C7	130.4 (2)	C21—C20—C18	121.47 (19)
N1—C8—C7	105.31 (17)	C21—C20—H20	119.3
N1—C9—N2	111.61 (16)	C18—C20—H20	119.3
N1—C9—H9A	109.3	C20—C21—C15	119.78 (19)
N2—C9—H9A	109.3	C20—C21—H21	120.1
N1—C9—H9B	109.3	C15—C21—H21	120.1
N2—C9—H9B	109.3
C8—N1—C1—O1	−179.12 (19)	C1—N1—C9—N2	108.7 (2)
C9—N1—C1—O1	−11.4 (3)	C10—N2—C9—N1	104.0 (2)
C8—N1—C1—C2	0.2 (2)	C14—N2—C9—N1	−76.5 (2)
C9—N1—C1—C2	167.94 (17)	C14—N2—C10—C11	1.0 (3)
O1—C1—C2—C3	0.9 (4)	C9—N2—C10—C11	−179.58 (18)
N1—C1—C2—C3	−178.3 (2)	N2—C10—C11—C12	−1.3 (3)
O1—C1—C2—C7	179.2 (2)	C10—C11—C12—C13	0.6 (3)
N1—C1—C2—C7	−0.1 (2)	C11—C12—C13—C14	0.4 (3)
C7—C2—C3—C4	−0.4 (3)	C10—N2—C14—C13	0.0 (3)
C1—C2—C3—C4	177.63 (19)	C9—N2—C14—C13	−179.44 (18)
C2—C3—C4—C5	−0.2 (3)	C12—C13—C14—N2	−0.7 (3)
C3—C4—C5—C6	0.7 (3)	O3—S1—C15—C21	−30.90 (19)
C4—C5—C6—C7	−0.5 (3)	O5—S1—C15—C21	89.57 (17)
C5—C6—C7—C2	−0.2 (3)	O4—S1—C15—C21	−150.81 (16)
C5—C6—C7—C8	−177.4 (2)	O3—S1—C15—C16	150.97 (16)
C3—C2—C7—C6	0.6 (3)	O5—S1—C15—C16	−88.55 (17)
C1—C2—C7—C6	−177.78 (19)	O4—S1—C15—C16	31.06 (19)
C3—C2—C7—C8	178.36 (18)	C21—C15—C16—C17	−0.7 (3)
C1—C2—C7—C8	−0.1 (2)	S1—C15—C16—C17	177.49 (15)
C1—N1—C8—O2	179.69 (19)	C15—C16—C17—C18	0.8 (3)
C9—N1—C8—O2	11.9 (3)	C16—C17—C18—C20	−0.1 (3)
C1—N1—C8—C7	−0.2 (2)	C16—C17—C18—C19	178.17 (19)
C9—N1—C8—C7	−168.02 (17)	C17—C18—C20—C21	−0.8 (3)
C6—C7—C8—O2	−2.3 (4)	C19—C18—C20—C21	−179.02 (19)
C2—C7—C8—O2	−179.7 (2)	C18—C20—C21—C15	1.0 (3)
C6—C7—C8—N1	177.6 (2)	C16—C15—C21—C20	−0.2 (3)
C2—C7—C8—N1	0.2 (2)	S1—C15—C21—C20	−178.34 (15)
C8—N1—C9—N2	−84.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···Cg1i	0.95	2.70	3.531 (2)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯Cg1i	0.95	2.70	3.531 (2)	147

Symmetry code: (i) . Cg1 is the centroid of the N2/C10–C14 ring.