4-Methyl-N-[(E)-4-methyl-1-(4-methyl-phenyl-sulfon-yl)-1,2-dihydropyridin-2-yl-idene]benzene-sulfonamide.

The reaction of 2-(amino-meth-yl)pyridine and 4-toluene-sulfonyl chloride in CH(2)Cl(2) at pH 8 led to the title compound, C(20)H(20)N(2)O(4)S(2). The aromatic rings are almost perpendicular to each other and the dihedral angles between the aromatic ring planes are 74.33 (9) (central pyridine versus benzene ring of the tosyl group bonded to the imine functionality), 73.77 (6) (pyridine versus benzene ring of the tosyl group bonded to pyridinic N atom) and 79.83 (9)° (benzene rings of tosyl groups). In the crystal structure, inter-molecular aromatic π-π stacking inter-actions [centroid-centroid separation = 3.6274 (14) Å] help to consolidate the packing.

Related literature

For sulfonamide compounds, see: Maren (1967 ▶); Supuran et al. (1999 ▶); Culf et al. (1997 ▶); Kremer et al. (2006 ▶). For 2-amino-methyl­pyridine sulfonamide derivatives, see: Beloso et al. (2003 ▶, 2004 ▶, 2005 ▶, 2006 ▶). For related N and S-containing compounds, see: Tabatabaee et al. (2006 ▶, 2007 ▶, 2008 ▶, 2009 ▶).

Experimental

Crystal data

C20H20N2O4S2

M = 416.50

Orthorhombic,

a = 14.888 (1) Å

b = 13.884 (1) Å

c = 18.843 (1) Å

V = 3894.9 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.30 mm−1

T = 100 K

0.21 × 0.12 × 0.08 mm

Data collection

Stoe IPDS-2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.78, T max = 1.0

39760 measured reflections

3785 independent reflections

2634 reflections with I > 2σ(I)

R int = 0.139

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.094

S = 0.94

3785 reflections

301 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.28 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL-Plus (Sheldrick, 2008 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810025158/bh2287sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810025158/bh2287Isup2.hkl

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

C20H20N2O4S2	F(000) = 1744
Mr = 416.50	Dx = 1.421 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 15000 reflections
a = 14.888 (1) Å	θ = 2.2–25.9°
b = 13.884 (1) Å	µ = 0.30 mm−1
c = 18.843 (1) Å	T = 100 K
V = 3894.9 (4) Å3	Blocks, colorless
Z = 8	0.21 × 0.12 × 0.08 mm

Stoe IPDS-2 diffractometer	3785 independent reflections
Radiation source: fine-focus sealed tube	2634 reflections with I > 2σ(I)
graphite	Rint = 0.139
ω scans	θmax = 25.9°, θmin = 2.2°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −18→16
Tmin = 0.78, Tmax = 1.0	k = −17→17
39760 measured reflections	l = −23→23

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) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 0.94	w = 1/[σ2(Fo2) + (0.0461P)2] where P = (Fo2 + 2Fc2)/3
3785 reflections	(Δ/σ)max = 0.006
301 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.28 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
N1	0.05540 (13)	0.20334 (16)	0.60238 (10)	0.0345 (5)
C1	0.02054 (16)	0.17947 (17)	0.54034 (12)	0.0320 (5)
C2	−0.05445 (18)	0.12038 (19)	0.52422 (13)	0.0350 (6)
H21	−0.0872 (18)	0.094 (2)	0.5645 (14)	0.043 (8)*
C3	−0.07778 (16)	0.09601 (18)	0.45642 (13)	0.0363 (6)
C4	−0.02553 (18)	0.1336 (2)	0.40005 (14)	0.0404 (6)
H41	−0.0383 (19)	0.118 (2)	0.3541 (14)	0.047 (8)*
C5	0.04321 (18)	0.1926 (2)	0.41261 (13)	0.0380 (6)
H51	0.0800 (18)	0.224 (2)	0.3798 (14)	0.043 (8)*
N2	0.06665 (13)	0.21788 (15)	0.48155 (10)	0.0322 (5)
C6	−0.15554 (18)	0.0317 (2)	0.44075 (15)	0.0458 (7)
H61	−0.1993	0.0663	0.4115	0.074 (3)*
H62	−0.1840	0.0119	0.4853	0.074 (3)*
H63	−0.1344	−0.0255	0.4152	0.074 (3)*
S1	0.01200 (4)	0.17417 (5)	0.67754 (3)	0.03399 (16)
O1	−0.02748 (12)	0.07934 (12)	0.67874 (9)	0.0400 (4)
O2	0.08054 (11)	0.19323 (14)	0.72943 (8)	0.0437 (5)
C10	−0.07471 (16)	0.25859 (18)	0.69174 (11)	0.0311 (5)
C11	−0.05235 (19)	0.3552 (2)	0.70311 (12)	0.0378 (6)
H111	0.0090 (19)	0.375 (2)	0.7026 (13)	0.045 (8)*
C12	−0.1196 (2)	0.4205 (2)	0.71944 (14)	0.0423 (6)
H121	−0.1048 (18)	0.484 (2)	0.7293 (14)	0.045 (8)*
C13	−0.20904 (18)	0.3922 (2)	0.72532 (12)	0.0388 (6)
C14	−0.22968 (17)	0.2957 (2)	0.71211 (12)	0.0350 (6)
H141	−0.2888 (16)	0.2719 (17)	0.7150 (11)	0.026 (6)*
C15	−0.16385 (17)	0.22994 (19)	0.69476 (11)	0.0313 (5)
H151	−0.1737 (16)	0.1651 (19)	0.6852 (12)	0.031 (6)*
C16	−0.2808 (2)	0.4625 (2)	0.74675 (16)	0.0559 (8)
H161	−0.3267	0.4656	0.7096	0.074 (3)*
H162	−0.2541	0.5263	0.7534	0.074 (3)*
H163	−0.3084	0.4412	0.7913	0.074 (3)*
S2	0.15670 (4)	0.29710 (5)	0.49328 (3)	0.03332 (16)
O3	0.12874 (12)	0.36943 (12)	0.54198 (9)	0.0383 (4)
O4	0.17995 (12)	0.32336 (13)	0.42217 (8)	0.0397 (4)
C17	0.24203 (16)	0.22493 (17)	0.52834 (11)	0.0300 (5)
C18	0.29660 (16)	0.17449 (18)	0.48104 (12)	0.0333 (6)
H181	0.2828 (16)	0.1738 (18)	0.4335 (13)	0.035 (7)*
C19	0.36808 (17)	0.12187 (18)	0.50725 (13)	0.0345 (6)
H191	0.405 (2)	0.088 (2)	0.4766 (14)	0.049 (8)*
C20	0.38645 (17)	0.11905 (17)	0.57977 (12)	0.0316 (5)
C21	0.33018 (16)	0.17011 (19)	0.62528 (12)	0.0336 (5)
H211	0.3456 (18)	0.173 (2)	0.6730 (15)	0.046 (7)*
C22	0.25832 (17)	0.22302 (19)	0.60086 (12)	0.0334 (6)
H221	0.2183 (18)	0.259 (2)	0.6317 (14)	0.043 (7)*
C23	0.46446 (17)	0.0628 (2)	0.60856 (13)	0.0384 (6)
H231	0.5158	0.0691	0.5764	0.074 (3)*
H232	0.4477	−0.0053	0.6126	0.074 (3)*
H233	0.4807	0.0877	0.6555	0.074 (3)*

	U11	U22	U33	U12	U13	U23
N1	0.0301 (10)	0.0417 (12)	0.0318 (10)	−0.0014 (10)	0.0027 (8)	−0.0025 (9)
C1	0.0284 (12)	0.0321 (13)	0.0356 (12)	0.0052 (11)	0.0012 (10)	−0.0011 (10)
C2	0.0329 (13)	0.0338 (14)	0.0384 (13)	0.0031 (11)	0.0002 (11)	0.0002 (11)
C3	0.0323 (13)	0.0329 (14)	0.0437 (13)	0.0061 (11)	−0.0053 (11)	−0.0057 (11)
C4	0.0411 (15)	0.0447 (16)	0.0353 (14)	0.0059 (13)	−0.0082 (12)	−0.0085 (12)
C5	0.0384 (14)	0.0430 (16)	0.0326 (13)	0.0047 (13)	0.0020 (11)	−0.0025 (12)
N2	0.0314 (10)	0.0358 (12)	0.0294 (10)	−0.0007 (9)	0.0006 (8)	−0.0034 (8)
C6	0.0406 (15)	0.0410 (16)	0.0558 (16)	0.0016 (13)	−0.0085 (13)	−0.0077 (12)
S1	0.0302 (3)	0.0412 (4)	0.0305 (3)	0.0009 (3)	0.0005 (2)	0.0024 (3)
O1	0.0422 (10)	0.0346 (10)	0.0432 (9)	0.0007 (8)	0.0044 (8)	0.0043 (8)
O2	0.0350 (9)	0.0611 (13)	0.0352 (9)	0.0020 (9)	−0.0040 (7)	0.0040 (8)
C10	0.0358 (13)	0.0365 (14)	0.0208 (11)	−0.0008 (11)	0.0012 (9)	0.0022 (10)
C11	0.0359 (14)	0.0424 (16)	0.0351 (13)	−0.0063 (13)	0.0019 (11)	0.0016 (11)
C12	0.0512 (17)	0.0374 (16)	0.0385 (14)	−0.0017 (14)	0.0019 (12)	0.0003 (12)
C13	0.0440 (15)	0.0449 (17)	0.0274 (11)	0.0086 (13)	0.0011 (11)	0.0028 (11)
C14	0.0322 (13)	0.0482 (16)	0.0246 (11)	0.0000 (12)	0.0016 (9)	0.0058 (11)
C15	0.0329 (13)	0.0378 (15)	0.0232 (11)	−0.0031 (11)	−0.0014 (9)	0.0027 (10)
C16	0.0565 (19)	0.054 (2)	0.0571 (17)	0.0186 (16)	0.0006 (14)	−0.0007 (15)
S2	0.0315 (3)	0.0334 (3)	0.0350 (3)	0.0006 (3)	0.0029 (2)	0.0004 (3)
O3	0.0372 (10)	0.0310 (10)	0.0465 (10)	0.0024 (8)	0.0042 (8)	−0.0071 (8)
O4	0.0376 (10)	0.0441 (11)	0.0374 (9)	0.0026 (8)	0.0052 (7)	0.0088 (8)
C17	0.0292 (12)	0.0297 (13)	0.0311 (12)	−0.0023 (10)	0.0014 (9)	0.0005 (9)
C18	0.0338 (13)	0.0396 (15)	0.0264 (12)	0.0009 (11)	0.0032 (10)	0.0005 (10)
C19	0.0375 (14)	0.0353 (14)	0.0308 (12)	0.0042 (11)	0.0038 (11)	−0.0011 (11)
C20	0.0316 (13)	0.0293 (14)	0.0339 (12)	−0.0029 (11)	0.0008 (10)	0.0001 (10)
C21	0.0318 (13)	0.0415 (15)	0.0277 (11)	−0.0034 (11)	−0.0007 (10)	−0.0012 (10)
C22	0.0317 (13)	0.0377 (15)	0.0310 (12)	−0.0028 (11)	0.0046 (10)	−0.0065 (11)
C23	0.0371 (14)	0.0396 (15)	0.0384 (13)	−0.0002 (12)	−0.0057 (11)	−0.0002 (11)

N1—C1	1.321 (3)	C13—C14	1.397 (4)
N1—S1	1.609 (2)	C13—C16	1.502 (4)
C1—N2	1.408 (3)	C14—C15	1.379 (4)
C1—C2	1.418 (4)	C14—H141	0.94 (2)
C2—C3	1.367 (3)	C15—H151	0.93 (3)
C2—H21	0.98 (3)	C16—H161	0.9800
C3—C4	1.416 (4)	C16—H162	0.9800
C3—C6	1.492 (4)	C16—H163	0.9800
C4—C5	1.333 (4)	S2—O3	1.4225 (17)
C4—H41	0.91 (3)	S2—O4	1.4310 (17)
C5—N2	1.390 (3)	S2—C17	1.748 (2)
C5—H51	0.93 (3)	C17—C22	1.388 (3)
N2—S2	1.748 (2)	C17—C18	1.395 (3)
C6—H61	0.9800	C18—C19	1.382 (3)
C6—H62	0.9800	C18—H181	0.92 (2)
C6—H63	0.9800	C19—C20	1.394 (3)
S1—O2	1.4378 (18)	C19—H191	0.93 (3)
S1—O1	1.4421 (19)	C20—C21	1.393 (3)
S1—C10	1.764 (3)	C20—C23	1.501 (3)
C10—C15	1.387 (3)	C21—C22	1.377 (4)
C10—C11	1.398 (4)	C21—H211	0.93 (3)
C11—C12	1.385 (4)	C22—H221	0.97 (3)
C11—H111	0.96 (3)	C23—H231	0.9800
C12—C13	1.392 (4)	C23—H232	0.9800
C12—H121	0.93 (3)	C23—H233	0.9800
C1—N1—S1	123.92 (18)	C15—C14—C13	121.4 (2)
N1—C1—N2	114.2 (2)	C15—C14—H141	116.4 (15)
N1—C1—C2	130.1 (2)	C13—C14—H141	122.2 (14)
N2—C1—C2	115.7 (2)	C14—C15—C10	120.0 (2)
C3—C2—C1	122.9 (2)	C14—C15—H151	125.1 (16)
C3—C2—H21	120.4 (16)	C10—C15—H151	114.9 (15)
C1—C2—H21	116.6 (15)	C13—C16—H161	109.5
C2—C3—C4	118.1 (2)	C13—C16—H162	109.5
C2—C3—C6	122.0 (2)	H161—C16—H162	109.5
C4—C3—C6	119.9 (2)	C13—C16—H163	109.5
C5—C4—C3	121.0 (2)	H161—C16—H163	109.5
C5—C4—H41	118.5 (18)	H162—C16—H163	109.5
C3—C4—H41	120.5 (18)	O3—S2—O4	119.67 (11)
C4—C5—N2	120.9 (2)	O3—S2—C17	111.94 (11)
C4—C5—H51	128.4 (16)	O4—S2—C17	108.91 (11)
N2—C5—H51	110.7 (17)	O3—S2—N2	107.53 (10)
C5—N2—C1	121.2 (2)	O4—S2—N2	103.14 (10)
C5—N2—S2	117.98 (17)	C17—S2—N2	104.15 (11)
C1—N2—S2	120.84 (15)	C22—C17—C18	121.2 (2)
C3—C6—H61	109.5	C22—C17—S2	120.67 (18)
C3—C6—H62	109.5	C18—C17—S2	118.02 (17)
H61—C6—H62	109.5	C19—C18—C17	119.1 (2)
C3—C6—H63	109.5	C19—C18—H181	121.0 (16)
H61—C6—H63	109.5	C17—C18—H181	119.8 (16)
H62—C6—H63	109.5	C18—C19—C20	121.1 (2)
O2—S1—O1	116.53 (11)	C18—C19—H191	120.5 (17)
O2—S1—N1	105.50 (11)	C20—C19—H191	118.4 (17)
O1—S1—N1	114.05 (11)	C21—C20—C19	118.1 (2)
O2—S1—C10	107.09 (11)	C21—C20—C23	120.5 (2)
O1—S1—C10	107.82 (11)	C19—C20—C23	121.4 (2)
N1—S1—C10	105.09 (11)	C22—C21—C20	122.2 (2)
C15—C10—C11	119.8 (2)	C22—C21—H211	119.6 (17)
C15—C10—S1	121.1 (2)	C20—C21—H211	117.9 (17)
C11—C10—S1	119.09 (19)	C21—C22—C17	118.4 (2)
C12—C11—C10	119.3 (3)	C21—C22—H221	123.4 (15)
C12—C11—H111	120.0 (17)	C17—C22—H221	118.3 (15)
C10—C11—H111	120.5 (17)	C20—C23—H231	109.5
C11—C12—C13	121.7 (3)	C20—C23—H232	109.5
C11—C12—H121	119.6 (17)	H231—C23—H232	109.5
C13—C12—H121	118.7 (17)	C20—C23—H233	109.5
C12—C13—C14	117.8 (2)	H231—C23—H233	109.5
C12—C13—C16	121.2 (3)	H232—C23—H233	109.5
C14—C13—C16	121.0 (3)