2-(Mesitylmethyl-sulfan-yl)pyridine N-oxide-18-crown-6 (2/1).

In the title compound, 2C(15)H(17)NOS·C(12)H(24)O(6), the asymmetric unit consists of one N-oxide derivative and one-half of the 18-crown-6 ether, which lies on an inversion centre. In the crown ether, the O-C-C-O torsion angles indicate a gauche conformation of the ethyl-eneoxy units, while the C-O-C-C torsion angles indicate planarity of these segments. In the N-oxide unit, the dihedral angle between the pyridine and benzene rings is 85.88 (12)°. The crystal packing is stabilized by weak C-H⋯O hydrogen bonds and C-H⋯π inter-actions.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For the biological activities of N-oxide derivatives, see: Bovin et al.(1992 ▶); Katsuyuki et al.(1991 ▶); Leonard et al.(1955 ▶); Lobana & Bhatia (1989 ▶); Symons & West (1985 ▶). For related structures, see: Jebas et al.(2005 ▶); Ravindran Durai Nayagam et al. (2008 ▶).

Experimental

Crystal data

2C15H17NOS·C12H24O6

M = 783.02

Monoclinic,

a = 8.050 (2) Å

b = 18.1903 (18) Å

c = 14.424 (4) Å

β = 93.475 (14)°

V = 2108.3 (8) Å3

Z = 2

Cu Kα radiation

μ = 1.57 mm−1

T = 298 (2) K

0.26 × 0.22 × 0.19 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.95, T max = 0.99 (expected range = 0.712–0.742)

3999 measured reflections

3999 independent reflections

2846 reflections with I > 2σ(I)

3 standard reflections frequency: 60 min intensity decay: 3%

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.132

S = 1.02

3999 reflections

247 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808012403/ci2589sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808012403/ci2589Isup2.hkl

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

2C15H17NOS·C12H24O6	F000 = 840
Mr = 783.02	Dx = 1.233 Mg m−3
Monoclinic, P21/c	Cu Kα radiation λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 8.050 (2) Å	θ = 26–41º
b = 18.1903 (18) Å	µ = 1.57 mm−1
c = 14.424 (4) Å	T = 298 (2) K
β = 93.475 (14)º	Block, colourless
V = 2108.3 (8) Å3	0.26 × 0.22 × 0.19 mm
Z = 2

Enraf–Nonius CAD-4 diffractometer	Rint = 0
Monochromator: graphite	θmax = 70.1º
T = 298(2) K	θmin = 3.9º
ω/2θ scans	h = 0→9
Absorption correction: ψ scan(North et al., 1968)	k = 0→22
Tmin = 0.95, Tmax = 0.99	l = −17→17
3999 measured reflections	3 standard reflections
3999 independent reflections	every 60 min
2846 reflections with I > 2σ(I)	intensity decay: 3%

Refinement on F2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0563P)2 + 0.3138P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.049	(Δ/σ)max < 0.001
wR(F2) = 0.132	Δρmax = 0.21 e Å−3
S = 1.03	Δρmin = −0.25 e Å−3
3999 reflections	Extinction correction: none
247 parameters

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.

	x	y	z	Uiso*/Ueq
C1	0.7135 (3)	0.08450 (12)	0.27904 (15)	0.0427 (5)
C2	0.7560 (3)	0.01163 (13)	0.29202 (16)	0.0478 (6)
H2	0.7162	−0.0144	0.3415	0.057*
C3	0.8569 (3)	−0.02246 (14)	0.23183 (18)	0.0571 (7)
H3	0.8865	−0.0715	0.2411	0.069*
C4	0.9142 (4)	0.01540 (15)	0.1584 (2)	0.0637 (7)
H4	0.9813	−0.0077	0.1169	0.076*
C5	0.8717 (3)	0.08740 (16)	0.1468 (2)	0.0637 (7)
H5	0.9106	0.1134	0.097	0.076*
N6	0.7742 (3)	0.12176 (11)	0.20600 (15)	0.0532 (5)
O7	0.7329 (3)	0.19062 (10)	0.19510 (16)	0.0837 (7)
S8	0.58479 (9)	0.13969 (3)	0.34265 (5)	0.0552 (2)
C9	0.5267 (3)	0.07413 (12)	0.43059 (17)	0.0498 (6)
H9A	0.4587	0.0353	0.402	0.06*
H9B	0.6256	0.0521	0.4606	0.06*
C10	0.4303 (3)	0.11466 (12)	0.50103 (16)	0.0437 (5)
C11	0.5156 (3)	0.15214 (12)	0.57329 (17)	0.0459 (5)
C12	0.4274 (3)	0.19058 (13)	0.63763 (17)	0.0502 (6)
H12	0.4853	0.2164	0.6849	0.06*
C13	0.2556 (3)	0.19120 (13)	0.63282 (17)	0.0494 (6)
C14	0.1730 (3)	0.15298 (13)	0.56197 (18)	0.0510 (6)
H14	0.0573	0.1521	0.5591	0.061*
C15	0.2554 (3)	0.11556 (13)	0.49443 (17)	0.0481 (6)
C16	0.7035 (3)	0.15389 (16)	0.5834 (2)	0.0643 (7)
H16A	0.7387	0.1898	0.6292	0.096*
H16B	0.7466	0.1666	0.5249	0.096*
H16C	0.7444	0.1063	0.6025	0.096*
C17	0.1631 (4)	0.23629 (17)	0.7009 (2)	0.0729 (9)
H17A	0.2288	0.2399	0.7585	0.109*
H17B	0.059	0.213	0.7115	0.109*
H17C	0.1428	0.2846	0.6759	0.109*
C18	0.1546 (4)	0.07817 (17)	0.4161 (2)	0.0760 (9)
H18A	0.1669	0.0258	0.4218	0.114*
H18B	0.1935	0.0939	0.3577	0.114*
H18C	0.0394	0.091	0.419	0.114*
C19	0.3730 (4)	0.40558 (17)	0.5469 (2)	0.0732 (8)
H19A	0.4134	0.4271	0.491	0.088*
H19B	0.446	0.3652	0.5657	0.088*
O20	0.2098 (2)	0.37888 (10)	0.52814 (12)	0.0592 (5)
C21	0.2021 (4)	0.32669 (14)	0.45558 (19)	0.0601 (7)
H21A	0.2724	0.2849	0.4727	0.072*
H21B	0.2421	0.3485	0.3997	0.072*
C22	0.0265 (4)	0.30186 (14)	0.43774 (19)	0.0604 (7)
H22A	0.0223	0.2597	0.3966	0.072*
H22B	−0.02	0.2877	0.4956	0.072*
O23	−0.0651 (2)	0.36052 (10)	0.39661 (13)	0.0635 (5)
C24	−0.2386 (4)	0.34718 (16)	0.3842 (2)	0.0701 (8)
H24A	−0.2832	0.3347	0.4432	0.084*
H24B	−0.2596	0.3064	0.3417	0.084*
C25	−0.3196 (4)	0.41482 (17)	0.3459 (2)	0.0710 (8)
H25A	−0.267	0.4298	0.2901	0.085*
H25B	−0.4362	0.4051	0.3294	0.085*
O26	−0.3054 (2)	0.47147 (10)	0.41232 (12)	0.0593 (5)
C27	−0.3763 (4)	0.53832 (17)	0.3785 (2)	0.0751 (9)
H27A	−0.4904	0.5298	0.3555	0.09*
H27B	−0.3146	0.5562	0.3274	0.09*

	U11	U22	U33	U12	U13	U23
C1	0.0446 (12)	0.0398 (11)	0.0441 (12)	−0.0009 (10)	0.0063 (10)	0.0024 (10)
C2	0.0595 (15)	0.0396 (12)	0.0446 (13)	0.0021 (11)	0.0072 (11)	0.0024 (10)
C3	0.0721 (18)	0.0430 (13)	0.0575 (16)	0.0097 (12)	0.0141 (13)	−0.0013 (11)
C4	0.0701 (18)	0.0579 (16)	0.0655 (18)	0.0079 (14)	0.0232 (14)	−0.0043 (14)
C5	0.0668 (17)	0.0661 (17)	0.0609 (16)	0.0010 (14)	0.0273 (14)	0.0083 (14)
N6	0.0555 (12)	0.0434 (11)	0.0623 (13)	0.0026 (9)	0.0160 (10)	0.0114 (9)
O7	0.1030 (17)	0.0471 (11)	0.1058 (17)	0.0174 (11)	0.0451 (13)	0.0281 (11)
S8	0.0691 (4)	0.0367 (3)	0.0622 (4)	0.0080 (3)	0.0234 (3)	0.0054 (3)
C9	0.0619 (15)	0.0363 (12)	0.0526 (14)	0.0007 (11)	0.0147 (12)	0.0009 (10)
C10	0.0471 (13)	0.0355 (11)	0.0494 (13)	0.0004 (9)	0.0103 (10)	0.0027 (10)
C11	0.0416 (12)	0.0413 (12)	0.0554 (14)	0.0010 (10)	0.0094 (10)	0.0009 (10)
C12	0.0544 (15)	0.0465 (13)	0.0499 (14)	0.0031 (11)	0.0050 (11)	−0.0025 (11)
C13	0.0551 (15)	0.0455 (13)	0.0494 (14)	0.0106 (11)	0.0180 (11)	0.0104 (11)
C14	0.0405 (12)	0.0496 (14)	0.0639 (16)	0.0039 (11)	0.0109 (11)	0.0135 (12)
C15	0.0473 (13)	0.0403 (12)	0.0565 (14)	−0.0030 (10)	0.0026 (11)	0.0067 (11)
C16	0.0475 (15)	0.0646 (17)	0.0806 (19)	0.0003 (13)	0.0036 (13)	−0.0121 (15)
C17	0.084 (2)	0.0733 (19)	0.0652 (18)	0.0222 (16)	0.0339 (16)	0.0082 (15)
C18	0.0627 (18)	0.073 (2)	0.090 (2)	−0.0042 (15)	−0.0110 (16)	−0.0117 (18)
C19	0.0583 (17)	0.0603 (18)	0.101 (2)	0.0089 (14)	0.0081 (16)	0.0113 (17)
O20	0.0580 (11)	0.0578 (11)	0.0633 (11)	0.0006 (8)	0.0147 (9)	−0.0013 (9)
C21	0.0724 (18)	0.0469 (14)	0.0634 (17)	0.0101 (13)	0.0246 (14)	0.0093 (12)
C22	0.082 (2)	0.0395 (13)	0.0613 (16)	0.0011 (13)	0.0222 (14)	0.0054 (12)
O23	0.0668 (12)	0.0476 (10)	0.0768 (13)	−0.0066 (9)	0.0089 (10)	0.0110 (9)
C24	0.073 (2)	0.0585 (17)	0.079 (2)	−0.0173 (15)	0.0043 (16)	−0.0082 (15)
C25	0.0691 (19)	0.0725 (19)	0.0694 (19)	−0.0102 (16)	−0.0117 (15)	−0.0074 (16)
O26	0.0608 (11)	0.0588 (11)	0.0574 (11)	0.0024 (9)	−0.0048 (9)	0.0023 (9)
C27	0.0657 (19)	0.072 (2)	0.085 (2)	0.0026 (15)	−0.0183 (16)	0.0099 (17)

C1—N6	1.368 (3)	C16—H16C	0.96
C1—C2	1.379 (3)	C17—H17A	0.96
C1—S8	1.743 (2)	C17—H17B	0.96
C2—C3	1.373 (3)	C17—H17C	0.96
C2—H2	0.93	C18—H18A	0.96
C3—C4	1.367 (4)	C18—H18B	0.96
C3—H3	0.93	C18—H18C	0.96
C4—C5	1.362 (4)	C19—O20	1.411 (3)
C4—H4	0.93	C19—C27i	1.482 (4)
C5—N6	1.348 (3)	C19—H19A	0.97
C5—H5	0.93	C19—H19B	0.97
N6—O7	1.303 (3)	O20—C21	1.412 (3)
S8—C9	1.823 (2)	C21—C22	1.491 (4)
C9—C10	1.508 (3)	C21—H21A	0.97
C9—H9A	0.97	C21—H21B	0.97
C9—H9B	0.97	C22—O23	1.408 (3)
C10—C11	1.392 (3)	C22—H22A	0.97
C10—C15	1.406 (3)	C22—H22B	0.97
C11—C12	1.391 (3)	O23—C24	1.418 (3)
C11—C16	1.510 (3)	C24—C25	1.483 (4)
C12—C13	1.380 (3)	C24—H24A	0.97
C12—H12	0.93	C24—H24B	0.97
C13—C14	1.374 (4)	C25—O26	1.407 (3)
C13—C17	1.509 (3)	C25—H25A	0.97
C14—C15	1.389 (3)	C25—H25B	0.97
C14—H14	0.93	O26—C27	1.417 (3)
C15—C18	1.512 (4)	C27—C19i	1.482 (4)
C16—H16A	0.96	C27—H27A	0.97
C16—H16B	0.96	C27—H27B	0.97
N6—C1—C2	118.9 (2)	C13—C17—H17B	109.5
N6—C1—S8	111.80 (17)	H17A—C17—H17B	109.5
C2—C1—S8	129.24 (18)	C13—C17—H17C	109.5
C3—C2—C1	120.0 (2)	H17A—C17—H17C	109.5
C3—C2—H2	120	H17B—C17—H17C	109.5
C1—C2—H2	120	C15—C18—H18A	109.5
C4—C3—C2	120.2 (2)	C15—C18—H18B	109.5
C4—C3—H3	119.9	H18A—C18—H18B	109.5
C2—C3—H3	119.9	C15—C18—H18C	109.5
C5—C4—C3	119.1 (2)	H18A—C18—H18C	109.5
C5—C4—H4	120.5	H18B—C18—H18C	109.5
C3—C4—H4	120.5	O20—C19—C27i	110.6 (2)
N6—C5—C4	121.3 (2)	O20—C19—H19A	109.5
N6—C5—H5	119.4	C27i—C19—H19A	109.5
C4—C5—H5	119.4	O20—C19—H19B	109.5
O7—N6—C5	121.5 (2)	C27i—C19—H19B	109.5
O7—N6—C1	118.0 (2)	H19A—C19—H19B	108.1
C5—N6—C1	120.5 (2)	C19—O20—C21	111.8 (2)
C1—S8—C9	100.10 (11)	O20—C21—C22	109.3 (2)
C10—C9—S8	108.26 (15)	O20—C21—H21A	109.8
C10—C9—H9A	110	C22—C21—H21A	109.8
S8—C9—H9A	110	O20—C21—H21B	109.8
C10—C9—H9B	110	C22—C21—H21B	109.8
S8—C9—H9B	110	H21A—C21—H21B	108.3
H9A—C9—H9B	108.4	O23—C22—C21	108.1 (2)
C11—C10—C15	119.5 (2)	O23—C22—H22A	110.1
C11—C10—C9	119.6 (2)	C21—C22—H22A	110.1
C15—C10—C9	120.9 (2)	O23—C22—H22B	110.1
C12—C11—C10	119.8 (2)	C21—C22—H22B	110.1
C12—C11—C16	118.3 (2)	H22A—C22—H22B	108.4
C10—C11—C16	121.9 (2)	C22—O23—C24	114.2 (2)
C13—C12—C11	121.4 (2)	O23—C24—C25	108.2 (2)
C13—C12—H12	119.3	O23—C24—H24A	110.1
C11—C12—H12	119.3	C25—C24—H24A	110.1
C14—C13—C12	118.1 (2)	O23—C24—H24B	110.1
C14—C13—C17	121.6 (2)	C25—C24—H24B	110.1
C12—C13—C17	120.2 (3)	H24A—C24—H24B	108.4
C13—C14—C15	122.7 (2)	O26—C25—C24	109.7 (2)
C13—C14—H14	118.7	O26—C25—H25A	109.7
C15—C14—H14	118.7	C24—C25—H25A	109.7
C14—C15—C10	118.5 (2)	O26—C25—H25B	109.7
C14—C15—C18	119.1 (2)	C24—C25—H25B	109.7
C10—C15—C18	122.4 (2)	H25A—C25—H25B	108.2
C11—C16—H16A	109.5	C25—O26—C27	112.3 (2)
C11—C16—H16B	109.5	O26—C27—C19i	110.6 (2)
H16A—C16—H16B	109.5	O26—C27—H27A	109.5
C11—C16—H16C	109.5	C19i—C27—H27A	109.5
H16A—C16—H16C	109.5	O26—C27—H27B	109.5
H16B—C16—H16C	109.5	C19i—C27—H27B	109.5
C13—C17—H17A	109.5	H27A—C27—H27B	108.1
N6—C1—C2—C3	−0.3 (4)	C10—C11—C12—C13	1.5 (4)
S8—C1—C2—C3	178.2 (2)	C16—C11—C12—C13	−179.8 (2)
C1—C2—C3—C4	−0.7 (4)	C11—C12—C13—C14	−0.4 (4)
C2—C3—C4—C5	1.0 (4)	C11—C12—C13—C17	−177.1 (2)
C3—C4—C5—N6	−0.2 (5)	C12—C13—C14—C15	−1.6 (4)
C4—C5—N6—O7	−179.9 (3)	C17—C13—C14—C15	175.1 (2)
C4—C5—N6—C1	−0.8 (4)	C13—C14—C15—C10	2.4 (3)
C2—C1—N6—O7	−179.8 (2)	C13—C14—C15—C18	−176.9 (2)
S8—C1—N6—O7	1.4 (3)	C11—C10—C15—C14	−1.3 (3)
C2—C1—N6—C5	1.1 (4)	C9—C10—C15—C14	179.2 (2)
S8—C1—N6—C5	−177.7 (2)	C11—C10—C15—C18	178.0 (2)
N6—C1—S8—C9	179.41 (18)	C9—C10—C15—C18	−1.6 (4)
C2—C1—S8—C9	0.8 (3)	C27i—C19—O20—C21	178.4 (2)
C1—S8—C9—C10	172.97 (17)	C19—O20—C21—C22	−178.8 (2)
S8—C9—C10—C11	−83.8 (2)	O20—C21—C22—O23	70.4 (3)
S8—C9—C10—C15	95.8 (2)	C21—C22—O23—C24	−174.0 (2)
C15—C10—C11—C12	−0.6 (3)	C22—O23—C24—C25	176.6 (2)
C9—C10—C11—C12	179.0 (2)	O23—C24—C25—O26	−66.6 (3)
C15—C10—C11—C16	−179.3 (2)	C24—C25—O26—C27	178.2 (3)
C9—C10—C11—C16	0.3 (3)	C25—O26—C27—C19i	174.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O23ii	0.93	2.50	3.187 (3)	131
C16—H16A···O7iii	0.96	2.38	3.257 (4)	152
C27—H27A···Cg1iv	0.97	2.78	3.723 (4)	163
C21—H21A···Cg2	0.97	2.80	3.693 (3)	153
C2—H2···Cg2v	0.93	2.90	3.732 (3)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O23i	0.93	2.50	3.187 (3)	131
C16—H16A⋯O7ii	0.96	2.38	3.257 (4)	152
C27—H27A⋯Cg1iii	0.97	2.78	3.723 (4)	163
C21—H21A⋯Cg2	0.97	2.80	3.693 (3)	153
C2—H2⋯Cg2iv	0.93	2.90	3.732 (3)	150

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg1 and Cg2 are the centroids of the N6/C1–C5 and C10–C15 rings, respectively.