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Acta Cryst. (2013). E69, o219    [ doi:10.1107/S160053681205180X ]

3-Methyl-1-tosyl-1H-indole-2-carbaldehyde

P. Pradeep, S. Khorasani, C. B. de Koning and M. A. Fernandes

Abstract top

The title indole derivative, C17H15NO3S, crystallizes with two independent molecules in the asymmetric unit. The benzene ring of the tosyl group is almost perpedicular to the indole ring in both molecules, with interplanar angles of 82.60 (5)° and 81.82 (6)°. The two molecules are, as a consequence, able to form an almost centrosymmetric non-bonded dimer, in which the molecules are linked by pairs of C-H...[pi] interactions. The crystal structure displays a three-dimensional network of C-H...O interactions. A [pi]-[pi] interaction occurs between inversion-related indole rings with a centroid-centroid distance of 3.6774 (16) Å and an interplanar angle of 1.53 (15)°. This interaction leads to a stacking of molecules along the a axis.

Comment top

Indoles are heterocyclic compounds containing a pyrrole ring fused to a benzene ring at the a,b positions. Indole is an important biological heterocyclic system as it is present, for example, in the amino acid tryptophan. As a consequence, it is a biologically accepted pharmacophore. Derivatives possess a broad spectrum of biological activities (Sharma et al., 2010), for example indomethacin (a non-steroidal anti-inflammatory drug) would fit in this class. The title compound is part of our continuing efforts to synthesize indole-based derivatives (Pathak et al., 2006; Pelly et al. 2005)

The title organic compound (Fig. 1) crystallizes in the space group P-1 with two independent molecules in the asymmetric unit. The aromatic moieties [indole (C1—C8 and N1) and tosyl group (C11—C17)] in each molecule are orientated with respect to each other at an angle of 82.60 (5)° and 81.82 (6)° in molecules A and B, respectively. The crystal structure contains C—H···O, C—H···π and π···π interactions. The π···π interaction occurs over a Cg1···Cg2 distance of 3.6774 (16) Å between two indole rings [Cg1 = N1A—C1A—C2A—C3A—C4A; Cg2 = N1B—C1B—C2B—C3B—C4B] with an interplanar angle of 1.53 (15) ° (Fig. 2). This leads to a stacking of molecules along the a axis. The structure contains several C—H···π interactions which are shown in Fig. 2. A layer of A and B molecules along the (001) plane is given in Fig. 3 showing the relative orientation of the A and B molecules in the layer. Geometrical details for the C—H···π and C—H···O interactions are given in Table 1.

Related literature top

For studies of reactions involving indoles, see: Pathak et al. (2006); Pelly et al. (2005); Sharma et al. (2010). It is interesting to note that the reaction used to synthesize this product has been reported to be ineffective when carried out in acetone, see: Kothandaraman et al. (2011).

Experimental top

The title compound was synthesized by reaction of iodine (942 mg, 3.70 mmol) with N-(2-(2-hydroxybut-3-yn-2-yl)phenyl-4-methyl)benzenesulfonamide (584.9 mg,1.854 mmol) in the presence of methanol (20 ml) as a solvent. The resulting mixture was stirred for 6 h at 60°C. The reaction was then quenched by adding a saturated aq. solution of Na2S2O3 and extracted with ethyl acetate (3×20 mL). The combined organics were then washed with aq. NaHCO3 and brine, and dried over anhydrous Na2SO4. After removal of solvent, the left over residue was purified by flash column chromatography, with silica gel using a mixture of hexane and ethyl acetate (20:1) to give 3-methyl-1-tosyl-1H-indole-2-carbaldehyde (329 mg, 86%). Single crystals were grown by slow evaporation from dichloromethane.

Refinement top

All H atoms attached to carbon were positioned geometrically, and allowed to ride on their parent atoms, with C—H bond lengths of 0.95 Å (CH) or 0.98 Å (CH3), and isotropic displacement parameters set to 1.2 (CH) or 1.5 times (CH3) the Ueq of the parent atom.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-NT (Bruker, 2005); data reduction: SAINT-NT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and SCHAKAL-99 (Keller, 1999); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. C—H···π and π···π interactions in the title structure. C—H···π and π···π interactions are respectively indicated by dollar ($) or hash (#) signs.
[Figure 3] Fig. 3. A layer of molecules along the (001) plane, showing the orientation of the A and B molecules with respect to each other. Also shown are the interactions between the molecules which result in molecules A and B forming almost centrosymmetric C—H···π stabilized dimers.
3-Methyl-1-tosyl-1H-indole-2-carbaldehyde top
Crystal data top
C17H15NO3SZ = 4
Mr = 313.36F(000) = 656
Triclinic, P1Dx = 1.379 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.4276 (2) ÅCell parameters from 2992 reflections
b = 13.0126 (3) Åθ = 2.3–28.0°
c = 14.2522 (4) ŵ = 0.23 mm−1
α = 79.968 (2)°T = 173 K
β = 79.794 (2)°Plate, colourless
γ = 83.505 (2)°0.28 × 0.25 × 0.05 mm
V = 1509.25 (7) Å3
Data collection top
Bruker APEX-II CCD
diffractometer		3668 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.051
Graphite monochromatorθmax = 26.0°, θmin = 1.5°
φ and ω scansh = −10→10
16378 measured reflectionsk = −16→16
5936 independent reflectionsl = −17→17
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0581P)2]
where P = (Fo2 + 2Fc2)/3
5936 reflections(Δ/σ)max = 0.028
401 parametersΔρmax = 0.31 e Å−3
0 restraintsΔρmin = −0.27 e Å−3
Crystal data top
C17H15NO3Sγ = 83.505 (2)°
Mr = 313.36V = 1509.25 (7) Å3
Triclinic, P1Z = 4
a = 8.4276 (2) ÅMo Kα radiation
b = 13.0126 (3) ŵ = 0.23 mm−1
c = 14.2522 (4) ÅT = 173 K
α = 79.968 (2)°0.28 × 0.25 × 0.05 mm
β = 79.794 (2)°
Data collection top
Bruker APEX-II CCD
diffractometer		3668 reflections with I > 2σ(I)
16378 measured reflectionsRint = 0.051
5936 independent reflectionsθmax = 26.0°
Refinement top
R[F2 > 2σ(F2)] = 0.049H-atom parameters constrained
wR(F2) = 0.126Δρmax = 0.31 e Å−3
S = 1.01Δρmin = −0.27 e Å−3
5936 reflectionsAbsolute structure: ?
401 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C1A−0.1003 (3)0.1746 (2)0.32889 (17)0.0336 (6)
C2A−0.0243 (3)0.2622 (2)0.32277 (19)0.0378 (7)
C3A0.0263 (3)0.2996 (2)0.22233 (19)0.0377 (6)
C4A−0.0216 (3)0.2323 (2)0.16787 (18)0.0351 (6)
C5A0.0136 (3)0.2468 (2)0.06829 (19)0.0440 (7)
H5A−0.01720.19990.03190.053*
C6A0.0963 (4)0.3335 (3)0.0240 (2)0.0577 (9)
H6A0.12250.3464−0.04440.069*
C7A0.1418 (4)0.4021 (3)0.0776 (2)0.0621 (9)
H7A0.19750.46100.04500.075*
C8A0.1078 (4)0.3861 (2)0.1755 (2)0.0529 (8)
H8A0.13920.43320.21140.063*
C9A−0.0073 (4)0.3179 (2)0.4035 (2)0.0558 (8)
H9A−0.06900.28460.46380.084*
H9B−0.04880.39140.38940.084*
H9C0.10710.31410.41000.084*
C10A−0.1948 (4)0.1188 (2)0.41602 (18)0.0440 (7)
H10A−0.28670.08620.40940.053*
C11A0.0869 (3)−0.0205 (2)0.19507 (17)0.0324 (6)
C12A0.1566 (3)−0.0613 (2)0.27611 (18)0.0368 (6)
H12A0.0971−0.05800.33880.044*
C13A0.3128 (3)−0.1065 (2)0.2650 (2)0.0426 (7)
H13A0.3609−0.13390.32060.051*
C14A0.4018 (3)−0.1130 (2)0.1740 (2)0.0398 (7)
C15A0.3290 (3)−0.0719 (2)0.0937 (2)0.0426 (7)
H15A0.3877−0.07630.03090.051*
C16A0.1733 (3)−0.0251 (2)0.10334 (18)0.0375 (6)
H16A0.12560.00380.04780.045*
C17A0.5725 (3)−0.1633 (2)0.1625 (2)0.0585 (9)
H17A0.6351−0.12910.10300.088*
H17B0.5712−0.23780.15930.088*
H17C0.6222−0.15590.21790.088*
O1A−0.1603 (3)0.11289 (18)0.49508 (14)0.0689 (7)
O2A−0.1671 (2)0.05043 (15)0.11669 (12)0.0436 (5)
O3A−0.2055 (2)−0.02049 (14)0.29029 (12)0.0422 (5)
S1A−0.11298 (8)0.03517 (5)0.20793 (4)0.03321 (18)
N1A−0.1070 (2)0.15447 (16)0.23392 (13)0.0316 (5)
C1B0.5657 (3)0.3352 (2)0.19951 (17)0.0356 (6)
C2B0.4829 (3)0.2483 (2)0.22155 (19)0.0384 (7)
C3B0.4422 (3)0.2264 (2)0.32444 (19)0.0375 (6)
C4B0.5034 (3)0.3020 (2)0.36399 (17)0.0345 (6)
C5B0.4824 (4)0.3024 (2)0.46271 (19)0.0474 (8)
H5B0.52270.35480.48870.057*
C6B0.4001 (4)0.2230 (3)0.5211 (2)0.0602 (9)
H6B0.38360.22080.58910.072*
C7B0.3405 (4)0.1461 (3)0.4838 (2)0.0656 (10)
H7B0.28450.09260.52650.079*
C8B0.3613 (4)0.1465 (2)0.3863 (2)0.0536 (8)
H8B0.32150.09330.36110.064*
C9B0.4467 (4)0.1824 (2)0.1536 (2)0.0588 (9)
H9D0.34860.21280.12770.088*
H9E0.43000.11140.18800.088*
H9F0.53760.17950.10050.088*
C10B0.6480 (4)0.3793 (2)0.1047 (2)0.0568 (9)
H10B0.73400.42180.10140.068*
C11B0.4026 (3)0.5558 (2)0.28498 (18)0.0350 (6)
C12B0.2877 (4)0.5569 (2)0.3677 (2)0.0465 (7)
H12B0.31290.52450.42900.056*
C13B0.1363 (4)0.6062 (2)0.3589 (2)0.0510 (8)
H13B0.05680.60700.41510.061*
C14B0.0965 (3)0.6543 (2)0.2710 (2)0.0446 (7)
C15B0.2131 (3)0.6505 (2)0.1895 (2)0.0441 (7)
H15B0.18750.68220.12810.053*
C16B0.3649 (3)0.6017 (2)0.19591 (19)0.0379 (6)
H16B0.44340.59950.13940.045*
C17B−0.0688 (4)0.7093 (3)0.2647 (3)0.0652 (10)
H17D−0.06980.74950.20000.098*
H17E−0.09560.75680.31270.098*
H17F−0.14880.65740.27750.098*
O1B0.6121 (3)0.3644 (2)0.03045 (15)0.0846 (8)
O2B0.7045 (2)0.53596 (15)0.20847 (15)0.0543 (6)
O3B0.6359 (2)0.49819 (16)0.38571 (14)0.0553 (6)
S1B0.59748 (9)0.49595 (6)0.29261 (5)0.0408 (2)
N1B0.5867 (2)0.36954 (16)0.28676 (14)0.0337 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.0385 (16)0.0350 (16)0.0275 (14)0.0018 (12)−0.0051 (11)−0.0089 (11)
C2A0.0366 (16)0.0349 (17)0.0434 (16)0.0010 (13)−0.0083 (13)−0.0109 (12)
C3A0.0357 (16)0.0298 (15)0.0460 (16)−0.0025 (12)−0.0032 (13)−0.0049 (12)
C4A0.0327 (15)0.0343 (16)0.0349 (15)−0.0017 (12)−0.0013 (12)−0.0008 (12)
C5A0.0482 (18)0.0459 (19)0.0333 (15)−0.0037 (14)−0.0031 (13)0.0025 (13)
C6A0.060 (2)0.059 (2)0.0407 (17)−0.0007 (17)0.0054 (16)0.0130 (16)
C7A0.062 (2)0.044 (2)0.071 (2)−0.0155 (17)0.0048 (18)0.0116 (17)
C8A0.053 (2)0.0361 (18)0.066 (2)−0.0110 (15)−0.0048 (16)−0.0005 (15)
C9A0.062 (2)0.056 (2)0.058 (2)−0.0030 (17)−0.0125 (16)−0.0293 (16)
C10A0.059 (2)0.0413 (18)0.0276 (15)0.0027 (14)−0.0013 (13)−0.0040 (12)
C11A0.0389 (15)0.0323 (15)0.0277 (13)−0.0090 (12)−0.0024 (11)−0.0083 (11)
C12A0.0443 (17)0.0370 (16)0.0307 (14)−0.0077 (13)−0.0074 (12)−0.0059 (11)
C13A0.0497 (18)0.0375 (17)0.0435 (17)−0.0041 (14)−0.0197 (14)−0.0018 (13)
C14A0.0390 (16)0.0305 (16)0.0533 (18)−0.0076 (13)−0.0069 (14)−0.0137 (13)
C15A0.0426 (17)0.0450 (18)0.0418 (16)−0.0056 (14)−0.0003 (13)−0.0169 (13)
C16A0.0448 (17)0.0401 (17)0.0308 (14)−0.0063 (13)−0.0090 (12)−0.0094 (12)
C17A0.0469 (19)0.048 (2)0.084 (2)−0.0030 (16)−0.0127 (17)−0.0167 (17)
O1A0.0877 (18)0.0860 (18)0.0295 (12)−0.0068 (14)−0.0072 (11)−0.0022 (11)
O2A0.0411 (11)0.0591 (13)0.0366 (10)−0.0050 (9)−0.0145 (9)−0.0149 (9)
O3A0.0450 (12)0.0386 (11)0.0412 (11)−0.0151 (9)0.0032 (9)−0.0041 (8)
S1A0.0365 (4)0.0362 (4)0.0287 (3)−0.0086 (3)−0.0042 (3)−0.0074 (3)
N1A0.0366 (13)0.0321 (13)0.0260 (11)−0.0076 (10)−0.0031 (9)−0.0036 (9)
C1B0.0363 (15)0.0395 (17)0.0295 (14)0.0024 (13)−0.0036 (12)−0.0069 (11)
C2B0.0344 (15)0.0402 (17)0.0426 (16)0.0026 (13)−0.0068 (12)−0.0154 (13)
C3B0.0338 (16)0.0306 (16)0.0464 (16)−0.0043 (12)−0.0017 (12)−0.0051 (12)
C4B0.0346 (15)0.0331 (15)0.0324 (14)−0.0002 (12)−0.0034 (12)0.0003 (11)
C5B0.059 (2)0.0468 (19)0.0331 (16)0.0010 (15)−0.0058 (14)−0.0032 (13)
C6B0.067 (2)0.070 (2)0.0305 (16)0.0054 (19)0.0038 (15)0.0071 (16)
C7B0.063 (2)0.053 (2)0.065 (2)−0.0080 (18)0.0075 (18)0.0186 (18)
C8B0.052 (2)0.0363 (18)0.068 (2)−0.0095 (15)−0.0011 (16)−0.0013 (15)
C9B0.066 (2)0.055 (2)0.065 (2)0.0038 (17)−0.0207 (17)−0.0315 (17)
C10B0.059 (2)0.057 (2)0.0419 (18)0.0087 (17)0.0091 (16)0.0001 (15)
C11B0.0393 (16)0.0286 (15)0.0396 (15)−0.0086 (12)−0.0067 (12)−0.0084 (11)
C12B0.059 (2)0.0482 (19)0.0365 (16)−0.0104 (16)−0.0064 (14)−0.0157 (13)
C13B0.049 (2)0.056 (2)0.0523 (19)−0.0076 (16)0.0029 (15)−0.0299 (16)
C14B0.0428 (17)0.0321 (17)0.067 (2)−0.0043 (13)−0.0127 (15)−0.0240 (14)
C15B0.0510 (19)0.0342 (17)0.0510 (18)−0.0056 (14)−0.0160 (15)−0.0084 (13)
C16B0.0416 (17)0.0337 (16)0.0388 (15)−0.0093 (13)−0.0035 (13)−0.0063 (12)
C17B0.049 (2)0.052 (2)0.101 (3)−0.0003 (17)−0.0153 (19)−0.0289 (19)
O1B0.0863 (19)0.128 (2)0.0307 (13)0.0125 (16)−0.0052 (12)−0.0067 (13)
O2B0.0395 (12)0.0464 (13)0.0713 (14)−0.0175 (10)0.0006 (10)0.0051 (10)
O3B0.0653 (14)0.0514 (14)0.0607 (13)−0.0082 (11)−0.0325 (11)−0.0154 (10)
S1B0.0401 (4)0.0355 (4)0.0493 (4)−0.0103 (3)−0.0117 (3)−0.0042 (3)
N1B0.0397 (13)0.0295 (13)0.0307 (12)−0.0058 (10)−0.0027 (10)−0.0023 (9)
Geometric parameters (Å, º) top
C1A—C2A1.353 (3)C1B—C2B1.356 (4)
C1A—N1A1.434 (3)C1B—N1B1.437 (3)
C1A—C10A1.473 (4)C1B—C10B1.457 (4)
C2A—C3A1.434 (4)C2B—C3B1.431 (4)
C2A—C9A1.497 (3)C2B—C9B1.490 (3)
C3A—C8A1.391 (4)C3B—C8B1.397 (4)
C3A—C4A1.400 (3)C3B—C4B1.401 (3)
C4A—C5A1.381 (3)C4B—C5B1.388 (3)
C4A—N1A1.422 (3)C4B—N1B1.416 (3)
C5A—C6A1.390 (4)C5B—C6B1.379 (4)
C5A—H5A0.9500C5B—H5B0.9500
C6A—C7A1.394 (4)C6B—C7B1.390 (4)
C6A—H6A0.9500C6B—H6B0.9500
C7A—C8A1.357 (4)C7B—C8B1.368 (4)
C7A—H7A0.9500C7B—H7B0.9500
C8A—H8A0.9500C8B—H8B0.9500
C9A—H9A0.9800C9B—H9D0.9800
C9A—H9B0.9800C9B—H9E0.9800
C9A—H9C0.9800C9B—H9F0.9800
C10A—O1A1.200 (3)C10B—O1B1.204 (4)
C10A—H10A0.9500C10B—H10B0.9500
C11A—C12A1.385 (3)C11B—C16B1.381 (4)
C11A—C16A1.387 (3)C11B—C12B1.388 (4)
C11A—S1A1.748 (3)C11B—S1B1.749 (3)
C12A—C13A1.373 (4)C12B—C13B1.378 (4)
C12A—H12A0.9500C12B—H12B0.9500
C13A—C14A1.390 (4)C13B—C14B1.379 (4)
C13A—H13A0.9500C13B—H13B0.9500
C14A—C15A1.391 (4)C14B—C15B1.386 (4)
C14A—C17A1.505 (4)C14B—C17B1.502 (4)
C15A—C16A1.377 (4)C15B—C16B1.373 (4)
C15A—H15A0.9500C15B—H15B0.9500
C16A—H16A0.9500C16B—H16B0.9500
C17A—H17A0.9800C17B—H17D0.9800
C17A—H17B0.9800C17B—H17E0.9800
C17A—H17C0.9800C17B—H17F0.9800
O2A—S1A1.4275 (17)O2B—S1B1.424 (2)
O3A—S1A1.4206 (18)O3B—S1B1.4262 (19)
S1A—N1A1.666 (2)S1B—N1B1.675 (2)
C2A—C1A—N1A109.9 (2)C2B—C1B—N1B109.8 (2)
C2A—C1A—C10A126.7 (2)C2B—C1B—C10B126.9 (3)
N1A—C1A—C10A122.2 (2)N1B—C1B—C10B122.5 (2)
C1A—C2A—C3A107.5 (2)C1B—C2B—C3B107.5 (2)
C1A—C2A—C9A127.6 (3)C1B—C2B—C9B127.6 (3)
C3A—C2A—C9A124.8 (2)C3B—C2B—C9B124.8 (3)
C8A—C3A—C4A119.6 (3)C8B—C3B—C4B119.1 (3)
C8A—C3A—C2A131.7 (3)C8B—C3B—C2B132.3 (3)
C4A—C3A—C2A108.7 (2)C4B—C3B—C2B108.5 (2)
C5A—C4A—C3A122.2 (2)C5B—C4B—C3B122.4 (2)
C5A—C4A—N1A130.6 (2)C5B—C4B—N1B129.9 (2)
C3A—C4A—N1A107.2 (2)C3B—C4B—N1B107.7 (2)
C4A—C5A—C6A116.6 (3)C6B—C5B—C4B116.6 (3)
C4A—C5A—H5A121.7C6B—C5B—H5B121.7
C6A—C5A—H5A121.7C4B—C5B—H5B121.7
C5A—C6A—C7A121.6 (3)C5B—C6B—C7B122.1 (3)
C5A—C6A—H6A119.2C5B—C6B—H6B118.9
C7A—C6A—H6A119.2C7B—C6B—H6B118.9
C8A—C7A—C6A121.1 (3)C8B—C7B—C6B120.9 (3)
C8A—C7A—H7A119.5C8B—C7B—H7B119.6
C6A—C7A—H7A119.5C6B—C7B—H7B119.6
C7A—C8A—C3A118.9 (3)C7B—C8B—C3B118.8 (3)
C7A—C8A—H8A120.5C7B—C8B—H8B120.6
C3A—C8A—H8A120.5C3B—C8B—H8B120.6
C2A—C9A—H9A109.5C2B—C9B—H9D109.5
C2A—C9A—H9B109.5C2B—C9B—H9E109.5
H9A—C9A—H9B109.5H9D—C9B—H9E109.5
C2A—C9A—H9C109.5C2B—C9B—H9F109.5
H9A—C9A—H9C109.5H9D—C9B—H9F109.5
H9B—C9A—H9C109.5H9E—C9B—H9F109.5
O1A—C10A—C1A122.6 (3)O1B—C10B—C1B123.0 (3)
O1A—C10A—H10A118.7O1B—C10B—H10B118.5
C1A—C10A—H10A118.7C1B—C10B—H10B118.5
C12A—C11A—C16A120.6 (2)C16B—C11B—C12B120.6 (3)
C12A—C11A—S1A120.00 (19)C16B—C11B—S1B119.2 (2)
C16A—C11A—S1A119.4 (2)C12B—C11B—S1B120.2 (2)
C13A—C12A—C11A119.4 (2)C13B—C12B—C11B118.5 (3)
C13A—C12A—H12A120.3C13B—C12B—H12B120.8
C11A—C12A—H12A120.3C11B—C12B—H12B120.8
C12A—C13A—C14A121.3 (2)C12B—C13B—C14B122.1 (3)
C12A—C13A—H13A119.3C12B—C13B—H13B119.0
C14A—C13A—H13A119.3C14B—C13B—H13B119.0
C13A—C14A—C15A118.3 (3)C13B—C14B—C15B118.1 (3)
C13A—C14A—C17A120.9 (3)C13B—C14B—C17B120.4 (3)
C15A—C14A—C17A120.8 (3)C15B—C14B—C17B121.4 (3)
C16A—C15A—C14A121.3 (3)C16B—C15B—C14B121.1 (3)
C16A—C15A—H15A119.4C16B—C15B—H15B119.4
C14A—C15A—H15A119.4C14B—C15B—H15B119.4
C15A—C16A—C11A119.2 (2)C15B—C16B—C11B119.6 (3)
C15A—C16A—H16A120.4C15B—C16B—H16B120.2
C11A—C16A—H16A120.4C11B—C16B—H16B120.2
C14A—C17A—H17A109.5C14B—C17B—H17D109.5
C14A—C17A—H17B109.5C14B—C17B—H17E109.5
H17A—C17A—H17B109.5H17D—C17B—H17E109.5
C14A—C17A—H17C109.5C14B—C17B—H17F109.5
H17A—C17A—H17C109.5H17D—C17B—H17F109.5
H17B—C17A—H17C109.5H17E—C17B—H17F109.5
O3A—S1A—O2A119.72 (11)O2B—S1B—O3B119.64 (13)
O3A—S1A—N1A105.70 (10)O2B—S1B—N1B106.31 (11)
O2A—S1A—N1A106.01 (11)O3B—S1B—N1B105.92 (11)
O3A—S1A—C11A109.47 (12)O2B—S1B—C11B108.81 (12)
O2A—S1A—C11A109.02 (11)O3B—S1B—C11B109.75 (13)
N1A—S1A—C11A106.01 (11)N1B—S1B—C11B105.42 (11)
C4A—N1A—C1A106.58 (19)C4B—N1B—C1B106.39 (19)
C4A—N1A—S1A121.62 (16)C4B—N1B—S1B121.72 (17)
C1A—N1A—S1A123.55 (17)C1B—N1B—S1B122.05 (17)
N1A—C1A—C2A—C3A−2.1 (3)N1B—C1B—C2B—C3B2.3 (3)
C10A—C1A—C2A—C3A−169.6 (2)C10B—C1B—C2B—C3B172.1 (3)
N1A—C1A—C2A—C9A172.6 (3)N1B—C1B—C2B—C9B−174.6 (3)
C10A—C1A—C2A—C9A5.2 (5)C10B—C1B—C2B—C9B−4.8 (5)
C1A—C2A—C3A—C8A179.6 (3)C1B—C2B—C3B—C8B−178.5 (3)
C9A—C2A—C3A—C8A4.6 (5)C9B—C2B—C3B—C8B−1.5 (5)
C1A—C2A—C3A—C4A0.2 (3)C1B—C2B—C3B—C4B−0.4 (3)
C9A—C2A—C3A—C4A−174.8 (3)C9B—C2B—C3B—C4B176.7 (3)
C8A—C3A—C4A—C5A2.0 (4)C8B—C3B—C4B—C5B−2.0 (4)
C2A—C3A—C4A—C5A−178.5 (2)C2B—C3B—C4B—C5B179.5 (2)
C8A—C3A—C4A—N1A−177.7 (2)C8B—C3B—C4B—N1B176.7 (2)
C2A—C3A—C4A—N1A1.9 (3)C2B—C3B—C4B—N1B−1.7 (3)
C3A—C4A—C5A—C6A−1.4 (4)C3B—C4B—C5B—C6B1.1 (4)
N1A—C4A—C5A—C6A178.1 (3)N1B—C4B—C5B—C6B−177.3 (3)
C4A—C5A—C6A—C7A0.2 (5)C4B—C5B—C6B—C7B−0.1 (5)
C5A—C6A—C7A—C8A0.5 (5)C5B—C6B—C7B—C8B−0.1 (5)
C6A—C7A—C8A—C3A0.0 (5)C6B—C7B—C8B—C3B−0.8 (5)
C4A—C3A—C8A—C7A−1.2 (4)C4B—C3B—C8B—C7B1.8 (4)
C2A—C3A—C8A—C7A179.4 (3)C2B—C3B—C8B—C7B179.8 (3)
C2A—C1A—C10A—O1A−34.5 (4)C2B—C1B—C10B—O1B24.1 (5)
N1A—C1A—C10A—O1A159.5 (3)N1B—C1B—C10B—O1B−167.3 (3)
C16A—C11A—C12A—C13A0.0 (4)C16B—C11B—C12B—C13B−1.0 (4)
S1A—C11A—C12A—C13A178.8 (2)S1B—C11B—C12B—C13B179.1 (2)
C11A—C12A—C13A—C14A−0.6 (4)C11B—C12B—C13B—C14B−0.3 (4)
C12A—C13A—C14A—C15A0.3 (4)C12B—C13B—C14B—C15B1.3 (4)
C12A—C13A—C14A—C17A−179.6 (2)C12B—C13B—C14B—C17B−178.6 (3)
C13A—C14A—C15A—C16A0.6 (4)C13B—C14B—C15B—C16B−1.0 (4)
C17A—C14A—C15A—C16A−179.6 (2)C17B—C14B—C15B—C16B178.9 (2)
C14A—C15A—C16A—C11A−1.1 (4)C14B—C15B—C16B—C11B−0.2 (4)
C12A—C11A—C16A—C15A0.8 (4)C12B—C11B—C16B—C15B1.2 (4)
S1A—C11A—C16A—C15A−178.0 (2)S1B—C11B—C16B—C15B−178.84 (19)
C12A—C11A—S1A—O3A−35.0 (2)C16B—C11B—S1B—O2B20.3 (2)
C16A—C11A—S1A—O3A143.9 (2)C12B—C11B—S1B—O2B−159.7 (2)
C12A—C11A—S1A—O2A−167.7 (2)C16B—C11B—S1B—O3B153.0 (2)
C16A—C11A—S1A—O2A11.2 (2)C12B—C11B—S1B—O3B−27.1 (3)
C12A—C11A—S1A—N1A78.6 (2)C16B—C11B—S1B—N1B−93.4 (2)
C16A—C11A—S1A—N1A−102.6 (2)C12B—C11B—S1B—N1B86.6 (2)
C5A—C4A—N1A—C1A177.3 (3)C5B—C4B—N1B—C1B−178.3 (3)
C3A—C4A—N1A—C1A−3.0 (3)C3B—C4B—N1B—C1B3.1 (3)
C5A—C4A—N1A—S1A28.0 (4)C5B—C4B—N1B—S1B−32.0 (4)
C3A—C4A—N1A—S1A−152.42 (18)C3B—C4B—N1B—S1B149.36 (19)
C2A—C1A—N1A—C4A3.2 (3)C2B—C1B—N1B—C4B−3.4 (3)
C10A—C1A—N1A—C4A171.4 (2)C10B—C1B—N1B—C4B−173.7 (2)
C2A—C1A—N1A—S1A151.88 (19)C2B—C1B—N1B—S1B−149.54 (19)
C10A—C1A—N1A—S1A−40.0 (3)C10B—C1B—N1B—S1B40.1 (3)
O3A—S1A—N1A—C4A179.08 (18)O2B—S1B—N1B—C4B173.42 (18)
O2A—S1A—N1A—C4A−52.9 (2)O3B—S1B—N1B—C4B45.1 (2)
C11A—S1A—N1A—C4A62.9 (2)C11B—S1B—N1B—C4B−71.2 (2)
O3A—S1A—N1A—C1A34.9 (2)O2B—S1B—N1B—C1B−45.5 (2)
O2A—S1A—N1A—C1A163.00 (19)O3B—S1B—N1B—C1B−173.75 (19)
C11A—S1A—N1A—C1A−81.2 (2)C11B—S1B—N1B—C1B69.9 (2)
Hydrogen-bond geometry (Å, º) top
Cg3, Cg4, Cg5 and Cg6 are the centroids of the C11B–C16B, C3B–C8B, C3A–C8A and C11A–C16A rings, respectively.
D—H···AD—HH···AD···AD—H···A
C16B—H16B···O1Bi0.952.503.153 (3)126
C12A—H12A···O1Aii0.952.483.218 (3)134
C16A—H16A···O2Aiii0.952.523.220 (3)131
C17B—H17F···O2Biv0.982.533.396 (4)147
C8A—H8A···Cg30.952.873.804 (3)167
C9A—H9C···Cg40.982.803.726 (4)158
C9B—H9D···Cg50.982.653.576 (4)158
C9B—H9E···Cg60.982.953.755 (4)140
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, −y, −z+1; (iii) −x, −y, −z; (iv) x−1, y, z.
Hydrogen-bond geometry (Å, º) top
Cg3, Cg4, Cg5 and Cg6 are the centroids of the C11B–C16B, C3B–C8B, C3A–C8A and C11A–C16A rings, respectively.
D—H···AD—HH···AD···AD—H···A
C16B—H16B···O1Bi0.952.503.153 (3)126
C12A—H12A···O1Aii0.952.483.218 (3)134
C16A—H16A···O2Aiii0.952.523.220 (3)131
C17B—H17F···O2Biv0.982.533.396 (4)147
C8A—H8A···Cg30.952.873.804 (3)167
C9A—H9C···Cg40.982.803.726 (4)158
C9B—H9D···Cg50.982.653.576 (4)158
C9B—H9E···Cg60.982.953.755 (4)140
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, −y, −z+1; (iii) −x, −y, −z; (iv) x−1, y, z.
Acknowledgements top

This work was supported by the University of the Witwatersrand and National Research Foundation, Pretoria.

references
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