supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers Open access

at2565 scheme

Acta Cryst. (2008). E64, o1036-o1037    [ doi:10.1107/S1600536808013081 ]

2,4,6-Tris(1-oxo-2-pyridylsulfanylmethyl)mesitylene methanol solvate

B. Ravindran Durai Nayagam, S. R. Jebas, C. Ravi Samuelraj and D. Schollmeyer

Abstract top

In the title compound, C27H27N3O3S3·CH4O, the dihedral angles formed by the mesitylene ring with the three oxopyridyl rings are 89.6 (1), 75.5 (1) and 80.69 (1)°, indicating that all three are nearly perpendicular to the mesitylene ring. Intramolecular C-H...S hydrogen bonds generate S(6) ring motifs. The crystal structure is stabilized by intramolecular C-H...S and intermolecular C-H...O hydrogen bonds and weak C-H...[pi] interactions.

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 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 bond lengths and angles agree well with the 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 meistylene ring is planar with the maximum deviation from planarity being -0.036 (1) Å. The dihedral angle formed by the meistylene ring with the oxopyridinium rings (C1–C5/N6) 89.6 (1) °; (C21–C25/N26) 75.5 (1) ° and (C30–C34/N35) 80.69 (1) ° respectively, indicating that all the three oxopyridinium rings are perpendicular to the meistylene ring.

Intramolecular C—H···S hydrogen bonds generate S(6)S(6) ring motifs. The crystal structure is stabilized by intramolecular C—H···S and intermolecular C—H··· O hydrogen bonds and weak C—H···π interactions (Table 1, where Cg1 is the centroid of the ring C10-C15).

Related literature top

For related literature on the biological activity of N-oxides see: Lobana et al., (1989); Symons & West (1985); Katsuyuki et al. (1991); Bovin et al. (1992); Leonard et al.(1955). For related literature on N-oxides see: Jebas et al. (2005); Ravindran et al. (2008). For bond-length data, see: Allen et al. (1987); Jebas et al. (2005); Ravindran et al. (2008). For hydrogen-bond motifs, see: Bernstein et al. (1995). Cg1 is the centroid of the ring C10–C15.

Experimental top

A mixture of tris(bromomethyl)mesitylene (0.399 g, 1 mmol) and 1-hydroxypyridine-2-thione sodium salt (0.448 g, 3 mmol) 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 (0.494 g, 92%). The compound was recrystallized from chloroform-methanol (1:2 v/v).

Refinement top

H atoms were positioned geometrically [C—H = 0.93 (aromatic), 0.96 Å (methyl) 0.97 Å (methylene), and 0.82Å O—H] and refined using a riding model, with Uiso(H) = 1.2 or -1.5Ueq(C).

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
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atomic numbering scheme.
2,4,6-Tris(1-oxo-2-pyridylsulfanylmethyl)mesitylene methanol solvate top
Crystal data top
C27H27N3O3S3·CH4OF000 = 1200
Mr = 569.74Dx = 1.372 Mg m−3
Monoclinic, P21/cCu Kα radiation
λ = 1.54178 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 11.9644 (17) Åθ = 61–69º
b = 14.9129 (8) ŵ = 2.78 mm−1
c = 15.467 (2) ÅT = 298 (2) K
β = 91.733 (7)ºBlock, colourless
V = 2758.4 (6) Å30.52 × 0.42 × 0.06 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer		θmax = 69.9º
Monochromator: graphiteθmin = 3.7º
ω/2θ scansh = 0→14
Absorption correction: ψ scan
(North et al., 1968)		k = −18→0
Tmin = 0.296, Tmax = 0.842l = −18→18
5226 measured reflections3 standard reflections
5226 independent reflections every 60 min
4156 reflections with I > 2σ(I) intensity decay: 3%
Rint = 0
Refinement top
Refinement on F212 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.051  w = 1/[σ2(Fo2) + (0.0834P)2 + 0.7123P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.150(Δ/σ)max = 0.001
S = 1.09Δρmax = 0.49 e Å−3
5226 reflectionsΔρmin = −0.32 e Å−3
347 parametersExtinction correction: none
Crystal data top
C27H27N3O3S3·CH4OV = 2758.4 (6) Å3
Mr = 569.74Z = 4
Monoclinic, P21/cCu Kα
a = 11.9644 (17) ŵ = 2.78 mm−1
b = 14.9129 (8) ÅT = 298 (2) K
c = 15.467 (2) Å0.52 × 0.42 × 0.06 mm
β = 91.733 (7)º
Data collection top
Enraf–Nonius CAD-4
diffractometer		4156 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)		Rint = 0
Tmin = 0.296, Tmax = 0.8423 standard reflections
5226 measured reflections every 60 min
5226 independent reflections intensity decay: 3%
Refinement top
R[F2 > 2σ(F2)] = 0.05112 restraints
wR(F2) = 0.150H-atom parameters constrained
S = 1.09Δρmax = 0.49 e Å−3
5226 reflectionsΔρmin = −0.32 e Å−3
347 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
xyzUiso*/Ueq
C10.3585 (2)0.25409 (17)−0.03619 (16)0.0411 (6)
C20.4031 (2)0.2831 (2)−0.11233 (17)0.0509 (7)
H20.44150.3372−0.1140.061*
C30.3906 (3)0.2318 (2)−0.18594 (19)0.0595 (8)
H30.41890.2516−0.23790.071*
C40.3357 (3)0.1508 (2)−0.1818 (2)0.0627 (8)
H40.32830.1149−0.23070.075*
C50.2921 (3)0.1234 (2)−0.1054 (2)0.0593 (8)
H50.25520.0686−0.10280.071*
N60.30179 (19)0.17480 (15)−0.03383 (15)0.0475 (5)
O70.2579 (2)0.15045 (15)0.03880 (14)0.0660 (6)
S80.36161 (6)0.30782 (4)0.06449 (4)0.04599 (19)
C90.4460 (2)0.40587 (17)0.04115 (15)0.0442 (6)
H9A0.52030.38790.02450.053*
H9B0.41170.4404−0.00570.053*
C100.4525 (2)0.46111 (16)0.12348 (15)0.0380 (5)
C110.3677 (2)0.52357 (17)0.13909 (16)0.0407 (5)
C120.3725 (2)0.57310 (16)0.21599 (16)0.0401 (5)
C130.4580 (2)0.55854 (16)0.27863 (16)0.0401 (5)
C140.5453 (2)0.49992 (16)0.25966 (15)0.0384 (5)
C150.5413 (2)0.44950 (16)0.18286 (15)0.0384 (5)
C160.2719 (3)0.5372 (2)0.07464 (19)0.0551 (7)
H16A0.28810.58710.03780.083*
H16B0.20470.54910.10490.083*
H16C0.26210.48410.04010.083*
C170.4548 (3)0.6036 (2)0.36637 (19)0.0588 (8)
H17A0.49660.65850.36520.088*
H17B0.4870.56450.40960.088*
H17C0.37860.61640.37990.088*
C180.6333 (3)0.3827 (2)0.16668 (19)0.0535 (7)
H18A0.60670.33840.1260.08*
H18B0.65520.3540.22010.08*
H18C0.69640.41330.14370.08*
C190.2853 (2)0.64413 (18)0.2303 (2)0.0489 (6)
H19A0.26880.67580.17660.059*
H19B0.3130.68720.27280.059*
S200.15895 (7)0.59076 (5)0.26844 (6)0.0598 (2)
C210.0714 (2)0.6832 (2)0.2755 (2)0.0534 (7)
C220.0959 (3)0.7726 (2)0.2634 (2)0.0627 (8)
H220.1670.78910.24650.075*
C230.0164 (3)0.8378 (3)0.2760 (3)0.0754 (10)
H230.03330.8980.26740.09*
C24−0.0876 (3)0.8128 (3)0.3012 (3)0.0837 (12)
H24−0.14120.85610.31210.1*
C25−0.1127 (3)0.7240 (3)0.3104 (3)0.0831 (12)
H25−0.18410.70720.32630.1*
N26−0.0351 (2)0.6605 (2)0.29666 (19)0.0687 (8)
O27−0.0591 (2)0.57455 (19)0.3027 (2)0.0984 (10)
C280.6442 (2)0.49055 (18)0.32203 (17)0.0450 (6)
H28A0.65310.54480.35610.054*
H28B0.7120.48130.29030.054*
S290.62016 (6)0.39480 (5)0.39312 (5)0.0517 (2)
C300.7555 (2)0.37491 (19)0.43343 (17)0.0475 (6)
C310.8492 (3)0.4281 (2)0.4247 (2)0.0604 (8)
H310.84310.48440.39930.073*
C320.9529 (3)0.3962 (3)0.4545 (3)0.0771 (10)
H321.01710.43010.44750.093*
C330.9589 (4)0.3142 (3)0.4943 (3)0.0871 (13)
H331.02780.29220.51420.104*
C340.8648 (4)0.2647 (3)0.5050 (2)0.0772 (11)
H340.87010.20940.53270.093*
N350.7633 (2)0.29458 (17)0.47588 (16)0.0572 (6)
O360.6727 (2)0.24782 (16)0.48565 (16)0.0756 (7)
O1L−0.1572 (5)0.5507 (4)0.1374 (4)0.205 (2)
H1L−0.120.51360.16490.308*
C2L−0.0867 (7)0.5996 (6)0.0829 (5)0.189 (3)
H2LA−0.05210.64780.1150.284*
H2LB−0.13010.62370.03510.284*
H2LC−0.030.56060.06150.284*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0480 (14)0.0322 (12)0.0432 (13)0.0010 (10)0.0013 (11)−0.0040 (10)
C20.0599 (16)0.0485 (16)0.0447 (14)−0.0036 (13)0.0087 (12)−0.0060 (12)
C30.0659 (19)0.066 (2)0.0471 (15)0.0032 (16)0.0085 (14)−0.0108 (14)
C40.0639 (18)0.065 (2)0.0594 (18)0.0085 (16)−0.0044 (15)−0.0287 (16)
C50.0639 (18)0.0428 (16)0.071 (2)−0.0009 (14)−0.0044 (15)−0.0194 (14)
N60.0517 (12)0.0371 (12)0.0536 (13)−0.0005 (10)0.0007 (10)−0.0030 (10)
O70.0869 (16)0.0497 (12)0.0620 (13)−0.0199 (11)0.0136 (12)0.0040 (10)
S80.0649 (4)0.0383 (3)0.0351 (3)−0.0115 (3)0.0081 (3)−0.0010 (2)
C90.0598 (16)0.0381 (14)0.0352 (12)−0.0108 (12)0.0078 (11)−0.0017 (10)
C100.0494 (14)0.0304 (12)0.0346 (12)−0.0079 (10)0.0060 (10)0.0004 (9)
C110.0465 (13)0.0332 (12)0.0425 (13)−0.0049 (10)0.0034 (11)0.0048 (10)
C120.0450 (13)0.0290 (12)0.0467 (13)−0.0001 (10)0.0082 (11)0.0028 (10)
C130.0497 (14)0.0294 (12)0.0416 (13)0.0001 (10)0.0079 (11)−0.0017 (10)
C140.0464 (13)0.0305 (12)0.0384 (12)−0.0026 (10)0.0037 (10)0.0024 (10)
C150.0477 (13)0.0293 (12)0.0387 (12)−0.0008 (10)0.0094 (10)0.0007 (9)
C160.0574 (17)0.0541 (17)0.0534 (16)0.0011 (14)−0.0053 (13)0.0049 (13)
C170.074 (2)0.0518 (17)0.0513 (16)0.0057 (15)0.0062 (14)−0.0164 (13)
C180.0585 (17)0.0464 (16)0.0557 (16)0.0127 (13)0.0063 (13)−0.0059 (13)
C190.0485 (14)0.0331 (13)0.0655 (17)0.0037 (11)0.0095 (13)0.0016 (12)
S200.0567 (4)0.0417 (4)0.0823 (5)0.0054 (3)0.0209 (4)0.0093 (3)
C210.0492 (15)0.0523 (17)0.0592 (17)0.0065 (13)0.0094 (13)0.0061 (13)
C220.0565 (17)0.0502 (17)0.082 (2)0.0055 (14)0.0066 (16)0.0005 (16)
C230.073 (2)0.054 (2)0.100 (3)0.0166 (18)0.006 (2)0.0046 (19)
C240.074 (2)0.078 (3)0.099 (3)0.032 (2)0.014 (2)0.010 (2)
C250.0563 (19)0.096 (3)0.099 (3)0.020 (2)0.0250 (19)0.020 (2)
N260.0583 (15)0.0674 (18)0.0815 (19)0.0050 (14)0.0231 (14)0.0188 (15)
O270.0813 (18)0.0709 (17)0.146 (3)−0.0036 (14)0.0488 (18)0.0273 (17)
C280.0495 (14)0.0383 (14)0.0471 (14)−0.0038 (11)−0.0007 (12)0.0030 (11)
S290.0522 (4)0.0503 (4)0.0524 (4)−0.0049 (3)−0.0013 (3)0.0111 (3)
C300.0598 (16)0.0425 (14)0.0399 (13)0.0037 (12)−0.0041 (12)−0.0029 (11)
C310.0605 (18)0.0562 (18)0.0639 (18)−0.0008 (15)−0.0104 (15)−0.0032 (15)
C320.058 (2)0.085 (3)0.087 (3)0.0017 (18)−0.0141 (18)−0.015 (2)
C330.080 (3)0.092 (3)0.087 (3)0.030 (2)−0.032 (2)−0.016 (2)
C340.101 (3)0.066 (2)0.064 (2)0.025 (2)−0.022 (2)0.0010 (17)
N350.0801 (18)0.0444 (14)0.0467 (13)0.0080 (13)−0.0035 (12)0.0002 (11)
O360.0988 (18)0.0528 (14)0.0755 (15)−0.0065 (13)0.0083 (14)0.0178 (12)
O1L0.213 (4)0.187 (4)0.214 (4)−0.065 (4)−0.012 (3)−0.012 (3)
C2L0.178 (5)0.210 (5)0.179 (5)−0.041 (4)−0.017 (4)0.006 (4)
Geometric parameters (Å, °) top
C1—N61.364 (3)C19—S201.822 (3)
C1—C21.377 (4)C19—H19A0.97
C1—S81.751 (2)C19—H19B0.97
C2—C31.376 (4)S20—C211.737 (3)
C2—H20.93C21—N261.368 (4)
C3—C41.377 (5)C21—C221.378 (4)
C3—H30.93C22—C231.379 (4)
C4—C51.368 (5)C22—H220.93
C4—H40.93C23—C241.368 (5)
C5—N61.349 (4)C23—H230.93
C5—H50.93C24—C251.366 (6)
N6—O71.306 (3)C24—H240.93
S8—C91.820 (3)C25—N261.348 (5)
C9—C101.517 (3)C25—H250.93
C9—H9A0.97N26—O271.318 (4)
C9—H9B0.97C28—S291.830 (3)
C10—C151.394 (4)C28—H28A0.97
C10—C111.404 (4)C28—H28B0.97
C11—C121.400 (4)S29—C301.742 (3)
C11—C161.510 (4)C30—N351.368 (4)
C12—C131.404 (4)C30—C311.384 (4)
C12—C191.508 (3)C31—C321.394 (5)
C13—C141.400 (3)C31—H310.93
C13—C171.516 (4)C32—C331.370 (6)
C14—C151.406 (3)C32—H320.93
C14—C281.510 (3)C33—C341.361 (6)
C15—C181.511 (4)C33—H330.93
C16—H16A0.96C34—N351.358 (4)
C16—H16B0.96C34—H340.93
C16—H16C0.96N35—O361.302 (4)
C17—H17A0.96O1L—C2L1.414 (9)
C17—H17B0.96O1L—H1L0.82
C17—H17C0.96C2L—H2LA0.96
C18—H18A0.96C2L—H2LB0.96
C18—H18B0.96C2L—H2LC0.96
C18—H18C0.96
N6—C1—C2120.1 (2)H18A—C18—H18C109.5
N6—C1—S8111.72 (18)H18B—C18—H18C109.5
C2—C1—S8128.2 (2)C12—C19—S20108.98 (18)
C3—C2—C1119.8 (3)C12—C19—H19A109.9
C3—C2—H2120.1S20—C19—H19A109.9
C1—C2—H2120.1C12—C19—H19B109.9
C2—C3—C4119.3 (3)S20—C19—H19B109.9
C2—C3—H3120.4H19A—C19—H19B108.3
C4—C3—H3120.4C21—S20—C19100.44 (13)
C5—C4—C3119.8 (3)N26—C21—C22118.4 (3)
C5—C4—H4120.1N26—C21—S20112.7 (2)
C3—C4—H4120.1C22—C21—S20128.9 (2)
N6—C5—C4120.9 (3)C21—C22—C23120.8 (3)
N6—C5—H5119.6C21—C22—H22119.6
C4—C5—H5119.6C23—C22—H22119.6
O7—N6—C5121.4 (2)C24—C23—C22119.0 (4)
O7—N6—C1118.5 (2)C24—C23—H23120.5
C5—N6—C1120.1 (3)C22—C23—H23120.5
C1—S8—C9100.86 (12)C25—C24—C23119.9 (3)
C10—C9—S8106.53 (16)C25—C24—H24120
C10—C9—H9A110.4C23—C24—H24120
S8—C9—H9A110.4N26—C25—C24120.7 (3)
C10—C9—H9B110.4N26—C25—H25119.7
S8—C9—H9B110.4C24—C25—H25119.7
H9A—C9—H9B108.6O27—N26—C25121.3 (3)
C15—C10—C11120.6 (2)O27—N26—C21117.7 (3)
C15—C10—C9120.3 (2)C25—N26—C21121.0 (3)
C11—C10—C9119.1 (2)C14—C28—S29108.76 (17)
C12—C11—C10119.0 (2)C14—C28—H28A109.9
C12—C11—C16120.1 (2)S29—C28—H28A109.9
C10—C11—C16120.9 (2)C14—C28—H28B109.9
C11—C12—C13121.0 (2)S29—C28—H28B109.9
C11—C12—C19119.0 (2)H28A—C28—H28B108.3
C13—C12—C19120.0 (2)C30—S29—C28100.76 (13)
C14—C13—C12119.0 (2)N35—C30—C31120.3 (3)
C14—C13—C17120.3 (2)N35—C30—S29111.7 (2)
C12—C13—C17120.7 (2)C31—C30—S29127.9 (2)
C13—C14—C15120.3 (2)C30—C31—C32119.2 (3)
C13—C14—C28119.9 (2)C30—C31—H31120.4
C15—C14—C28119.8 (2)C32—C31—H31120.4
C10—C15—C14119.8 (2)C33—C32—C31119.2 (4)
C10—C15—C18121.1 (2)C33—C32—H32120.4
C14—C15—C18119.1 (2)C31—C32—H32120.4
C11—C16—H16A109.5C34—C33—C32120.4 (4)
C11—C16—H16B109.5C34—C33—H33119.8
H16A—C16—H16B109.5C32—C33—H33119.8
C11—C16—H16C109.5N35—C34—C33121.1 (4)
H16A—C16—H16C109.5N35—C34—H34119.4
H16B—C16—H16C109.5C33—C34—H34119.4
C13—C17—H17A109.5O36—N35—C34121.7 (3)
C13—C17—H17B109.5O36—N35—C30118.7 (3)
H17A—C17—H17B109.5C34—N35—C30119.6 (3)
C13—C17—H17C109.5C2L—O1L—H1L109.5
H17A—C17—H17C109.5O1L—C2L—H2LA109.5
H17B—C17—H17C109.5O1L—C2L—H2LB109.5
C15—C18—H18A109.5H2LA—C2L—H2LB109.5
C15—C18—H18B109.5O1L—C2L—H2LC109.5
H18A—C18—H18B109.5H2LA—C2L—H2LC109.5
C15—C18—H18C109.5H2LB—C2L—H2LC109.5
N6—C1—C2—C3−0.2 (4)C13—C14—C15—C103.0 (3)
S8—C1—C2—C3−178.9 (2)C28—C14—C15—C10−177.1 (2)
C1—C2—C3—C4−1.6 (5)C13—C14—C15—C18−176.4 (2)
C2—C3—C4—C51.6 (5)C28—C14—C15—C183.5 (3)
C3—C4—C5—N60.2 (5)C11—C12—C19—S2081.2 (3)
C4—C5—N6—O7178.1 (3)C13—C12—C19—S20−99.9 (2)
C4—C5—N6—C1−1.9 (4)C12—C19—S20—C21−177.6 (2)
C2—C1—N6—O7−178.1 (3)C19—S20—C21—N26174.9 (2)
S8—C1—N6—O70.8 (3)C19—S20—C21—C22−5.5 (4)
C2—C1—N6—C51.9 (4)N26—C21—C22—C232.8 (5)
S8—C1—N6—C5−179.1 (2)S20—C21—C22—C23−176.7 (3)
N6—C1—S8—C9177.65 (19)C21—C22—C23—C240.3 (6)
C2—C1—S8—C9−3.5 (3)C22—C23—C24—C25−2.5 (7)
C1—S8—C9—C10178.14 (19)C23—C24—C25—N261.5 (7)
S8—C9—C10—C1592.9 (2)C24—C25—N26—O27−177.9 (4)
S8—C9—C10—C11−86.7 (2)C24—C25—N26—C211.8 (6)
C15—C10—C11—C12−1.1 (3)C22—C21—N26—O27175.8 (3)
C9—C10—C11—C12178.6 (2)S20—C21—N26—O27−4.5 (4)
C15—C10—C11—C16179.3 (2)C22—C21—N26—C25−3.9 (5)
C9—C10—C11—C16−1.0 (3)S20—C21—N26—C25175.7 (3)
C10—C11—C12—C13−2.6 (4)C13—C14—C28—S2994.8 (2)
C16—C11—C12—C13177.0 (2)C15—C14—C28—S29−85.0 (2)
C10—C11—C12—C19176.3 (2)C14—C28—S29—C30162.19 (18)
C16—C11—C12—C19−4.1 (4)C28—S29—C30—N35−168.0 (2)
C11—C12—C13—C146.3 (4)C28—S29—C30—C3110.1 (3)
C19—C12—C13—C14−172.5 (2)N35—C30—C31—C324.3 (5)
C11—C12—C13—C17−172.2 (2)S29—C30—C31—C32−173.7 (3)
C19—C12—C13—C179.0 (4)C30—C31—C32—C33−2.1 (5)
C12—C13—C14—C15−6.5 (3)C31—C32—C33—C34−0.3 (6)
C17—C13—C14—C15172.0 (2)C32—C33—C34—N350.7 (6)
C12—C13—C14—C28173.6 (2)C33—C34—N35—O36180.0 (3)
C17—C13—C14—C28−7.9 (4)C33—C34—N35—C301.4 (5)
C11—C10—C15—C140.8 (3)C31—C30—N35—O36177.5 (3)
C9—C10—C15—C14−178.9 (2)S29—C30—N35—O36−4.2 (3)
C11—C10—C15—C18−179.8 (2)C31—C30—N35—C34−3.9 (4)
C9—C10—C15—C180.5 (3)S29—C30—N35—C34174.3 (2)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1L—H1L···O270.822.412.804 (7)110
C16—H16A···O36i0.962.473.348 (4)152
C16—H16B···S200.962.683.420 (3)135
C18—H18B···S290.962.793.515 (3)133
C25—H25···O7ii0.932.443.147 (5)133
C28—H28A···O7i0.972.483.397 (3)157
C31—H31···O27iii0.932.353.107 (4)139
C2—H2···Cg1iv0.932.913.774 (3)154
C4—H4···Cg1v0.932.673.377 (3)134
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x, y+1/2, −z+1/2; (iii) x+1, y, z; (iv) −x+1, −y+1, −z; (v) x, −y−1/2, z−3/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1L—H1L···O270.822.412.804 (7)110
C16—H16A···O36i0.962.473.348 (4)152
C16—H16B···S200.962.683.420 (3)135
C18—H18B···S290.962.793.515 (3)133
C25—H25···O7ii0.932.443.147 (5)133
C28—H28A···O7i0.972.483.397 (3)157
C31—H31···O27iii0.932.353.107 (4)139
C2—H2···Cg1iv0.932.913.774 (3)154
C4—H4···Cg1v0.932.673.377 (3)134
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x, y+1/2, −z+1/2; (iii) x+1, y, z; (iv) −x+1, −y+1, −z; (v) x, −y−1/2, z−3/2.
Acknowledgements top

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

references
References top

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.

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.

Bovin, D. H. R., Crepon, E. & Zard, S. Z. (1992). Bull. Soc. Chim. Fr. 129, 145–150.

Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands.

Jebas, S. R., Balasubramanian, T., Ravidurai, B. & Kumaresan, S. (2005). Acta Cryst. E61, o2677–o2678.

Katsuyuki, N., Carter, B. J., Xu, J. & Hetch, S. M. (1991). J. Am. Chem. Soc. 113, 5099–5100.

Leonard, F., Barklay, F. A., Brown, E. V., Anderson, F. E. & Green, D. M. (1955). Antibiot. Chemother. pp. 261–264.

Lobana, T. S. & Bhatia, P. K. (1989). J. Sci. Ind. Res. 48, 394–401.

North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.

Ravindran Durai Nayagam, B., Jebas, S. R., Grace, S. & Schollmeyer, D. (2008). Acta Cryst. E64, o409.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Symons, M. C. R. & West, D.-X. (1985). J. Chem. Soc. Dalton Trans. pp. 379–381.