2-(Mesitylmethyl­sulfan­yl)pyridine N-oxide–18-crown-6 (2/1)

Ravindran Durai Nayagam, B.; Jebas, S.R.; Jebaraj Devadasan, J.; Schollmeyer, D.

doi:10.1107/S1600536808012403

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o976

doi:10.1107/S1600536808012403

Open

access

2-(Mesitylmethylsulfanyl)pyridine N-oxide–18-crown-6 (2/1)

B. Ravindran Durai Nayagam,^a ^* Samuel Robinson Jebas,^b J. Jebaraj Devadasan ^c and Dieter Schollmeyer ^d

^aDepartment of Chemistry, Popes College, Sawyerpuram 628 251, Tamil Nadu, India, ^bDepartment of Physics, Karunya University, Karunya Nagar, Coimbatore 641 114, India, ^cDepartment of Physics, Popes College, Sawyerpuram 628 251, Tamilnadu, India, and ^dInstitut für Organische Chemie, Universität Mainz, Duesbergweg 10-14, 55099 Mainz, Germany
^*Correspondence e-mail: b_ravidurai@yahoo.com

(Received 23 April 2008; accepted 28 April 2008; online 3 May 2008)

In the title compound, 2C₁₅H₁₇NOS·C₁₂H₂₄O₆, 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 ethyleneoxy 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 interactions.

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_r = 783.02
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.049
wR(F²) = 0.132
S = 1.02
3999 reflections
247 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.25 e Å⁻³

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⋯Cg2^iv	0.93	2.90	3.732 (3)	150
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) -x+1, -y, -z+1. Cg1 and Cg2 are the centroids of the N6/C1–C5 and C10–C15 rings, respectively.

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.

Supporting information

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

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

checkCIF report

Comment top

N-Oxides and their derivatives show a broad spectrum of biological activity, such as antifungal, antibacterial, antimicrobial and antibacterial activities (Lobana & Bhatia, 1989; Symons et al.,1985). These compounds are also found to be involved in DNA strand scission under physiological conditions (Katsuyuki et al., 1991; Bovin et al.1992). Pyridine N-oxides bearing a sulfur group in position 2 display significant antimicrobial activity (Leonard et al.,1955). In view of the importance of N-oxides, we have previously reported the crystal structures of N-oxide derivatives (Jebas et al., 2005; Ravindran Durai Nayagam et al., 2008). As an extension of our work on these derivatives, we report here the crystal structure of the title compound (Fig. 1).

The asymmetric unit of the title compound consists of one mono(1-oxopyridine 2-sulfanylmethyl)mesitylene molecule and one-half of a 18-crown 6-ether molecule, the other half being inversion related. The bond lengths and angles of the N-oxide moiety agree well with those observed in other N-oxide derivatives reported earlier (Jebas et al., 2005; Ravindran et al., 2008). The N—O bond length is in good agreement with the mean value of 1.304 (15) Å reported in the literature for pyridine N-oxides (Allen et al.,1987).

The oxopyridinium and benzene rings are planar to within ±0.006 (2) Å and ±0.012 (2) Å, respectively, and they form a dihedral angle of 85.88 (12)°, indicating that both the rings are perpendicular to each other. Atom O7 deviates from the plane of the pyridinium ring by 0.006 (2) Å.

The crystal packing is consolidated by weak C—H···π interactions involving the oxopyridinium (N6/C1–C5) and benzene rings (C10–15), and C—H···O hydrogen bonds (Table 1).

Related literature top

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). Cg1 and Cg2 are the centroids of the N6/C1–C5 and C10–C15 rings, respectively.

For related literature, see: Allen et al. (1987).

Experimental top

A mixture of mono(bromomethyl)mesitylene (0.213 g, 1 mmol), 1-hydroxypyridine-2-thione sodium salt (0.1491 mmol) and 18-crown-6-ether (0.250 g) in water (30 ml) and methanol (30 ml) was heated at 333 K with stirring for 30 min. The compound formed was filtered off and dried. The compound was recrystallized from a chloroform-methanol (1:1 v/v) solution.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: CAD-4 Software (Enraf–Nonius, 1989); 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 (Sheldrick, 2008.

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering scheme. Atoms labelled with the suffix A are generated by the symmetry operation (-x, 1-y, 1-z).
	Fig. 2. The crystal packing of the title compound, viewed along the a axis. Hydrogen bonds are shown as dashed lines.

2-(Mesitylmethylsulfanyl)pyridine N-oxide–18-crown-6 (1/1) top

Crystal data top

2C₁₅H₁₇NOS·C₁₂H₂₄O₆	F(000) = 840
M_r = 783.02	D_x = 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 = 26–41°
b = 18.1903 (18) Å	µ = 1.57 mm⁻¹
c = 14.424 (4) Å	T = 298 K
β = 93.475 (14)°	Block, colourless
V = 2108.3 (8) Å³	0.26 × 0.22 × 0.19 mm
Z = 2

Data collection top

Enraf–Nonius CAD-4 diffractometer	2846 reflections with I > 2σ(I)
Radiation source: rotating anode	R_int = 0
Graphite monochromator	θ_max = 70.1°, θ_min = 3.9°
ω/2θ scans	h = 0→9
Absorption correction: ψ scan (North et al., 1968)	k = 0→22
T_min = 0.95, T_max = 0.99	l = −17→17
3999 measured reflections	3 standard reflections every 60 min
3999 independent reflections	intensity decay: 3%

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.049	w = 1/[σ²(F_o²) + (0.0563P)² + 0.3138P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.132	(Δ/σ)_max < 0.001
S = 1.03	Δρ_max = 0.21 e Å⁻³
3999 reflections	Δρ_min = −0.25 e Å⁻³
247 parameters

Crystal data top

2C₁₅H₁₇NOS·C₁₂H₂₄O₆	V = 2108.3 (8) Å³
M_r = 783.02	Z = 2
Monoclinic, P2₁/c	Cu Kα radiation
a = 8.050 (2) Å	µ = 1.57 mm⁻¹
b = 18.1903 (18) Å	T = 298 K
c = 14.424 (4) Å	0.26 × 0.22 × 0.19 mm
β = 93.475 (14)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2846 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0
T_min = 0.95, T_max = 0.99	3 standard reflections every 60 min
3999 measured reflections	intensity decay: 3%
3999 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.132	H-atom parameters constrained
S = 1.03	Δρ_max = 0.21 e Å⁻³
3999 reflections	Δρ_min = −0.25 e Å⁻³
247 parameters

Special details top

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	0.7135 (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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

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···Cg1^iv	0.97	2.78	3.723 (4)	163
C21—H21A···Cg2	0.97	2.80	3.693 (3)	153
C2—H2···Cg2^v	0.93	2.90	3.732 (3)	150

Symmetry codes: (ii) −x+1, y−1/2, −z+1/2; (iii) x, −y+1/2, z+1/2; (iv) −x, y+1/2, −z+1/2; (v) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	2C₁₅H₁₇NOS·C₁₂H₂₄O₆
M_r	783.02
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	8.050 (2), 18.1903 (18), 14.424 (4)
β (°)	93.475 (14)
V (Å³)	2108.3 (8)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	1.57
Crystal size (mm)	0.26 × 0.22 × 0.19

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.95, 0.99
No. of measured, independent and observed [I > 2σ(I)] reflections	3999, 3999, 2846
R_int	0
(sin θ/λ)_max (Å⁻¹)	0.610

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.132, 1.03
No. of reflections	3999
No. of parameters	247
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.25

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008.

Hydrogen-bond geometry (Å, º) top

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···Cg2^iv	0.93	2.90	3.732 (3)	150

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x, −y+1/2, z+1/2; (iii) −x, y+1/2, −z+1/2; (iv) −x+1, −y, −z+1.

Acknowledgements

BRDN thanks the University Grants Commission, India, for a Teacher Fellowship.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–S19. CrossRef Web of Science Google Scholar
Bovin, D. H. R., Crepon, E. & Zard, S. Z. (1992). Bull. Soc. Chem. Fr. 129, 145–150. Google Scholar
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Jebas, S. R., Balasubramanian, T., Ravidurai, B. & Kumaresan, S. (2005). Acta Cryst. E61, o2677–o2678. Web of Science CSD CrossRef IUCr Journals Google Scholar
Katsuyuki, N., Carter, B. J., Xu, J. & Hetch, S. M. (1991). J. Am. Chem. Soc. 113, 5099–5100. Google Scholar
Leonard, F., Barklay, F. A., Brown, E. V., Anderson, F. E. & Green, D. M. (1955). Antibiot. Chemother. pp. 261–264. Google Scholar
Lobana, T. S. & Bhatia, P. K. (1989). J. Sci. Ind. Res. 48, 394–401. CAS Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Ravindran Durai Nayagam, B., Jebas, S. R., Grace, S. & Schollmeyer, D. (2008). Acta Cryst. E64, o409. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Symons, M. C. R. & West, D.-X. (1985). J Chem Soc Dalton Trans. pp. 379–381. CrossRef Web of Science Google Scholar