Crystal structure of 4-methyl-N-{(E)-meth­yl[(3aR,8aS)-2-oxo-3,3a,8,8a-tetra­hydro-2H-indeno­[1,2-d][1,3]oxazol-3-yl]-λ4-sulfanyl­idene}benzene­sulfonamide

Pereira, P.A.; Noll, B.C.; Oliver, A.G.; Silveira, G.P.

doi:10.1107/S2056989015024779

organic compounds

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ISSN: 2056-9890

Volume 71| Part 12| December 2015| Pages o1097-o1098

https://doi.org/10.1107/S2056989015024779

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Crystal structure of 4-methyl-N-{(E)-methyl[(3aR,8aS)-2-oxo-3,3a,8,8a-tetrahydro-2H-indeno[1,2-d][1,3]oxazol-3-yl]-λ⁴-sulfanylidene}benzenesulfonamide

Patrícia A. Pereira,^a Bruce C. Noll,^b Allen G. Oliver ^c and Gustavo P. Silveira ^a ^*

^aUniversidade Federal do Rio Grande do Sul, Instituto de Química Depto. Química Orgânica, Av. Bento Gonçalves, 9500 Agronomia, Porto Alegre RS 91501-970, Brazil, ^bBruker AXS Inc., 3456 E. Cheryl Parkway, Madison, WI 53711, USA, and ^cDepartment of Chemistry & Biochemistry, University of Notre Dame, Notre Dame IN 46556, USA
^*Correspondence e-mail: gustavo.silveira@iq.ufrgs.br

Edited by G. S. Nichol, University of Edinburgh, Scotland (Received 20 November 2015; accepted 24 December 2015; online 31 December 2015)

The formulation that the title compound, C₁₈H₁₈N₂O₄S₂, adopts is a zwitterionic core with the charge separated to the sulfilimine S and N atoms and is supported by the two different S—N bond distances about the sulfinimine N atom [1.594 (2) and 1.631 (2) Å, respectively] that are typical for such bonds. The notably unusual bond is S—N(oxazolidinone) [1.692 (2) Å] that is longer than a typical S—N bond [1.603 (18) Å, Mogul analysis; Macrae et al. (2008 ). J. Appl. Cryst. 41, 466–470]. The bond-angle sum about sulfilimine sulfur (308.35°) reflects the trigonal–pyramidal geometry of this atom. Two of the angles are less than 100°. Despite the pyramidalization of this sulfur, there are no significant intermolecular interactions, beyond usual van der Waals contacts, in the crystal packing.

Keywords: oxazolidinone; vinyl sulfonamide; crystal structure.

CCDC reference: 1444186

1. Related literature

Oxazolidinone sulfilimines are synthesized as precursors of vinyl sulfilimines which are used in the γ-lactamization reaction to generate chiral pyrrolidinones with medicinal chemistry interest. For the synthesis, see: Celentano & Colonna (1998 ); Silveira & Marino (2013 ). For sulfonyl oxazolidinone structures, see: Barbey et al. (2012 ); Berredjem et al. (2010 ); Bonnaud et al. (1987 ); Dewynter et al. (1997 ). For related vinyl sulfonamide chemistry, see: Silveira et al. (2013 ). For related oxazolidinone sulfinime structures, see: Silveira et al. (2012 , 2014 ). For the Hooft parameter, see: Hooft et al. (2008 ).

2. Experimental

2.1. Crystal data

C₁₈H₁₈N₂O₄S₂
M_r = 390.46
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.8841 (1) Å
b = 12.2326 (2) Å
c = 20.1911 (4) Å
V = 1700.30 (5) Å³
Z = 4
Cu Kα radiation
μ = 3.09 mm⁻¹
T = 100 K
0.42 × 0.40 × 0.34 mm

2.2. Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Krause et al., 2015 ) T_min = 0.701, T_max = 0.929
11963 measured reflections
3004 independent reflections
2984 reflections with I > 2σ(I)
R_int = 0.032

2.3. Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.070
S = 1.11
3004 reflections
237 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.36 e Å⁻³
Absolute structure: Flack x determined using 1183 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter: 0.052 (4)

Table 1
Selected geometric parameters (Å, °)

S1—N2	1.594 (2)
S1—N1	1.692 (2)
S1—C11	1.782 (3)
S2—O4	1.4430 (19)
S2—O3	1.451 (2)
S2—N2	1.631 (2)
S2—C12	1.768 (2)

N2—S1—N1	110.58 (11)
N2—S1—C11	99.43 (12)
N1—S1—C11	98.34 (11)
O4—S2—O3	117.24 (12)
O4—S2—N2	106.79 (12)
O3—S2—N2	112.27 (11)
O4—S2—C12	107.93 (11)
O3—S2—C12	108.03 (12)
N2—S2—C12	103.67 (12)

Data collection: APEX2 (Bruker, 2007 ); cell refinement: APEX2 and SAINT (Bruker, 2007); data reduction: SAINT and XPREP (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: XCIF (Sheldrick, 2008) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1444186

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2056989015024779/nk2234sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015024779/nk2234Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015024779/nk2234Isup3.cml

checkCIF report

Commentary top

Oxazolidinone sulfilimines are synthesized as precursors of vinyl sulfilimines which are used in the γ-lactamization reaction (Silveira & Marino, 2013) to generate chiral pyrrolidinones with medicinal chemistry interest. This compound represents one of only five other oxazolidinone compounds that incorporate an N—S—N backbone (Barbey et al., 2012; Berredjem et al., 2010; Bonnaud et al., 1987; Dewynter et al., 1997). It is the only reported structure that does not have a sulfonyl bridging the oxazolidinone ring to the second nitrogen atom. Related sulfur-containing oxazolidinones have been reported previously by us (Silveira et al., 2012; 2014). We have also reported a related sulfur-containing indole as a precursor of physostigmine alkaloid.(Silveira et al., 2013).

Synthesis and crystallization top

Following literature preparative methods (Celentano et al., 1998; Silveira & Marino, 2013): chloramine-T (951 mg, 4.18 mmol) and hexadecyltributylphosphonium bromide (100 mg, 0.20 mmol) were added to a solution of oxazolidinone sulfide (840 mg, 3.80 mmol) in toluene (25 mL) at 295 K. After overnight stirring, ethyl acetate (25 mL) was added and the mixture washed (2 x 30 mL water; 1 x 30 mL brine), dried over anhydrous sodium sulfate, filtered, and the mixture of solvents rota-evaporated at reduced pressure. To the resulting dry, crude product, silica gel (6 g) and methylene chloride (5 mL) were added and this slurry was rota-evaporated to yield the crude product on silica. This mixture was separated and purified through flash chromatography with elution (70% ethyl acetate / 30% hexanes). After slow evaporation of the ethyl acetate / hexanes elutant, the more polar sulfilimine was obtained as white crystals (688 mg). Two sulfilimine diasterioisomers were obtained in a ratio of 2.5:1 (total of 65% yield).

Refinement details top

The structure was modeled routinely with all non-hydrogen atoms included with an anistropic model. Hydrogen atoms were included in calculated positions riding on the atom to which they are bonded (C—H = 0.99 Å for methyl, 0.95 Å for methyne and aromatic. U_iso(H) was set = 1.5U_eq(C) for methyl and 1.2U_eq(C) for all others.

The absolute configuration from synthesis was confirmed by comparison of intensities of Friedel pairs of reflections yielding a Flack x parameter = 0.052 (4) (Parsons et al., 2013) and a Hooft y parameter = 0.050 (6) (Hooft et al., 2008).

Related literature top

For synthesis, see: Celentano & Colonna (1998); Silveira & Marino (2013). For sulfonyl oxazolidinone structures, see: Barbey et al. (2012); Berredjem et al. (2010); Bonnaud et al. (1987); Dewynter et al. (1997). For related vinyl sulfonamide chemistry, see: Silveira et al. (2013). For related oxazolidinone sulfinime structures, see: Silveira et al. (2012, 2014). For the Hooft parameter, see: Hooft et al. (2008).

Structure description top

Synthesis and crystallization top

Refinement details top

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 and SAINT (Bruker, 2007); data reduction: SAINT and XPREP (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: XCIF (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

Fig. 1. Labeling diagram of the title compound. Atomic displacement ellipsoids depicted at the 50% probability level. Hydrogen atoms depicted as spheres of an arbitrary radius.

4-Methyl-N-{(E)-methyl[(3aR,8aS)-2-oxo-3,3a,8,8a-tetrahydro-2H-indeno[1,2-d][1,3]oxazol-3-yl]-λ⁴-sulfanylidene}benzenesulfonamide top

Crystal data top

C₁₈H₁₈N₂O₄S₂	D_x = 1.525 Mg m⁻³
M_r = 390.46	Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 9988 reflections
a = 6.8841 (1) Å	θ = 4.2–69.2°
b = 12.2326 (2) Å	µ = 3.09 mm⁻¹
c = 20.1911 (4) Å	T = 100 K
V = 1700.30 (5) Å³	Parallelepiped, clear colorless
Z = 4	0.42 × 0.40 × 0.34 mm
F(000) = 816

Data collection top

Bruker SMART APEX CCD diffractometer	3004 independent reflections
Radiation source: fine-focus sealed tube, Siemens KFFCU2K-90	2984 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
Detector resolution: 8.33 pixels mm^-1	θ_max = 69.5°, θ_min = 4.2°
φ and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −14→14
T_min = 0.701, T_max = 0.929	l = −24→22
11963 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.028	H-atom parameters constrained
wR(F²) = 0.070	w = 1/[σ²(F_o²) + (0.0405P)² + 0.5066P] where P = (F_o² + 2F_c²)/3
S = 1.11	(Δ/σ)_max = 0.001
3004 reflections	Δρ_max = 0.29 e Å⁻³
237 parameters	Δρ_min = −0.36 e Å⁻³
0 restraints	Absolute structure: Flack x determined using 1183 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.052 (4)

Crystal data top

C₁₈H₁₈N₂O₄S₂	V = 1700.30 (5) Å³
M_r = 390.46	Z = 4
Orthorhombic, P2₁2₁2₁	Cu Kα radiation
a = 6.8841 (1) Å	µ = 3.09 mm⁻¹
b = 12.2326 (2) Å	T = 100 K
c = 20.1911 (4) Å	0.42 × 0.40 × 0.34 mm

Data collection top

Bruker SMART APEX CCD diffractometer	3004 independent reflections
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	2984 reflections with I > 2σ(I)
T_min = 0.701, T_max = 0.929	R_int = 0.032
11963 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	H-atom parameters constrained
wR(F²) = 0.070	Δρ_max = 0.29 e Å⁻³
S = 1.11	Δρ_min = −0.36 e Å⁻³
3004 reflections	Absolute structure: Flack x determined using 1183 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
237 parameters	Absolute structure parameter: 0.052 (4)
0 restraints

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.45871 (9)	0.55630 (5)	0.77781 (3)	0.00978 (15)
S2	0.67201 (9)	0.69687 (5)	0.85264 (3)	0.01185 (16)
O1	0.3825 (3)	0.25928 (14)	0.82183 (9)	0.0148 (4)
O2	0.6694 (3)	0.34297 (15)	0.80444 (9)	0.0176 (4)
O3	0.8276 (3)	0.63677 (15)	0.82056 (9)	0.0175 (4)
O4	0.6751 (3)	0.81443 (15)	0.84687 (9)	0.0185 (4)
N1	0.3831 (3)	0.44084 (18)	0.81606 (11)	0.0127 (5)
N2	0.4579 (3)	0.65675 (17)	0.82812 (11)	0.0132 (5)
C1	0.4975 (4)	0.3476 (2)	0.81239 (12)	0.0129 (5)
C2	0.1767 (4)	0.2920 (2)	0.82310 (13)	0.0136 (5)
H2	0.1106	0.2809	0.7795	0.016*
C3	0.0725 (4)	0.2347 (2)	0.87983 (13)	0.0148 (6)
H3A	−0.0688	0.2299	0.8713	0.018*
H3B	0.1246	0.1601	0.8867	0.018*
C4	0.1142 (4)	0.3068 (2)	0.93859 (13)	0.0124 (5)
C5	0.0916 (4)	0.2842 (2)	1.00541 (13)	0.0140 (6)
H5	0.0423	0.2157	1.0198	0.017*
C6	0.1431 (4)	0.3648 (2)	1.05088 (13)	0.0161 (6)
H6	0.1258	0.3512	1.0968	0.019*
C7	0.2188 (4)	0.4644 (2)	1.03076 (14)	0.0157 (6)
H7	0.2569	0.5170	1.0628	0.019*
C8	0.2393 (4)	0.4875 (2)	0.96324 (14)	0.0141 (5)
H8	0.2899	0.5558	0.9488	0.017*
C9	0.1843 (4)	0.4088 (2)	0.91814 (13)	0.0117 (5)
C10	0.1900 (4)	0.41298 (19)	0.84277 (13)	0.0116 (5)
H10	0.0833	0.4584	0.8234	0.014*
C11	0.2421 (4)	0.5860 (2)	0.73290 (13)	0.0149 (6)
H11A	0.1358	0.5997	0.7641	0.022*
H11B	0.2089	0.5237	0.7046	0.022*
H11C	0.2627	0.6510	0.7054	0.022*
C12	0.6749 (4)	0.6636 (2)	0.93784 (12)	0.0112 (5)
C13	0.6177 (4)	0.7407 (2)	0.98430 (13)	0.0136 (5)
H13	0.5750	0.8110	0.9706	0.016*
C14	0.6237 (4)	0.7138 (2)	1.05134 (13)	0.0153 (6)
H14	0.5858	0.7664	1.0834	0.018*
C15	0.6846 (4)	0.6107 (2)	1.07178 (13)	0.0157 (5)
C16	0.7366 (4)	0.5341 (2)	1.02403 (14)	0.0152 (6)
H16	0.7745	0.4628	1.0376	0.018*
C17	0.7344 (4)	0.5596 (2)	0.95710 (14)	0.0147 (5)
H17	0.7727	0.5071	0.9250	0.018*
C18	0.6940 (5)	0.5854 (2)	1.14496 (14)	0.0231 (6)
H18A	0.7504	0.5126	1.1514	0.035*
H18B	0.5628	0.5871	1.1637	0.035*
H18C	0.7752	0.6400	1.1672	0.035*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0116 (3)	0.0111 (3)	0.0066 (3)	−0.0007 (2)	0.0007 (2)	0.0007 (2)
S2	0.0124 (3)	0.0139 (3)	0.0093 (3)	−0.0022 (2)	0.0002 (2)	−0.0003 (2)
O1	0.0189 (10)	0.0105 (8)	0.0151 (9)	0.0019 (7)	0.0014 (7)	−0.0003 (7)
O2	0.0161 (9)	0.0186 (9)	0.0179 (9)	0.0046 (8)	0.0011 (8)	0.0004 (8)
O3	0.0116 (9)	0.0269 (10)	0.0140 (9)	−0.0032 (8)	0.0015 (8)	−0.0017 (8)
O4	0.0251 (10)	0.0161 (9)	0.0143 (9)	−0.0067 (8)	−0.0028 (8)	0.0036 (7)
N1	0.0141 (11)	0.0108 (10)	0.0133 (10)	0.0016 (9)	0.0039 (9)	0.0032 (9)
N2	0.0135 (11)	0.0141 (10)	0.0118 (10)	0.0004 (9)	0.0001 (9)	−0.0013 (9)
C1	0.0170 (14)	0.0137 (12)	0.0080 (12)	0.0023 (10)	0.0010 (10)	−0.0015 (10)
C2	0.0157 (13)	0.0129 (12)	0.0121 (12)	−0.0016 (11)	−0.0025 (11)	0.0014 (10)
C3	0.0173 (14)	0.0137 (12)	0.0134 (13)	−0.0036 (10)	−0.0014 (11)	0.0008 (11)
C4	0.0116 (11)	0.0133 (12)	0.0121 (12)	0.0020 (10)	−0.0014 (10)	0.0006 (11)
C5	0.0109 (12)	0.0164 (13)	0.0149 (13)	0.0002 (10)	0.0010 (10)	0.0059 (10)
C6	0.0122 (13)	0.0256 (14)	0.0106 (12)	0.0041 (11)	0.0015 (10)	0.0017 (11)
C7	0.0107 (13)	0.0218 (13)	0.0145 (13)	0.0024 (10)	−0.0001 (10)	−0.0054 (11)
C8	0.0114 (12)	0.0135 (12)	0.0174 (13)	0.0023 (10)	0.0033 (10)	−0.0010 (11)
C9	0.0090 (11)	0.0148 (12)	0.0111 (12)	0.0030 (10)	0.0025 (11)	0.0023 (10)
C10	0.0112 (12)	0.0120 (12)	0.0117 (12)	0.0003 (9)	0.0010 (11)	0.0030 (9)
C11	0.0168 (13)	0.0158 (12)	0.0122 (13)	−0.0026 (10)	−0.0057 (10)	0.0050 (10)
C12	0.0087 (11)	0.0168 (12)	0.0080 (11)	−0.0023 (10)	−0.0023 (10)	0.0024 (9)
C13	0.0106 (12)	0.0158 (12)	0.0142 (13)	−0.0013 (10)	−0.0004 (10)	0.0011 (11)
C14	0.0116 (12)	0.0215 (13)	0.0127 (12)	−0.0028 (10)	0.0013 (10)	−0.0013 (10)
C15	0.0111 (12)	0.0223 (13)	0.0136 (13)	−0.0054 (11)	−0.0024 (11)	0.0031 (11)
C16	0.0107 (12)	0.0156 (12)	0.0192 (13)	−0.0008 (10)	−0.0024 (10)	0.0050 (11)
C17	0.0103 (12)	0.0158 (12)	0.0180 (13)	−0.0003 (10)	0.0015 (10)	−0.0028 (11)
C18	0.0263 (16)	0.0287 (15)	0.0144 (13)	−0.0091 (12)	−0.0016 (13)	0.0049 (11)

Geometric parameters (Å, º) top

S1—N2	1.594 (2)	C7—C8	1.399 (4)
S1—N1	1.692 (2)	C7—H7	0.9500
S1—C11	1.782 (3)	C8—C9	1.378 (4)
S2—O4	1.4430 (19)	C8—H8	0.9500
S2—O3	1.451 (2)	C9—C10	1.523 (3)
S2—N2	1.631 (2)	C10—H10	1.0000
S2—C12	1.768 (2)	C11—H11A	0.9800
O1—C1	1.353 (3)	C11—H11B	0.9800
O1—C2	1.472 (3)	C11—H11C	0.9800
O2—C1	1.195 (3)	C12—C13	1.387 (4)
N1—C1	1.388 (3)	C12—C17	1.392 (4)
N1—C10	1.475 (3)	C13—C14	1.394 (4)
C2—C3	1.522 (4)	C13—H13	0.9500
C2—C10	1.535 (3)	C14—C15	1.391 (4)
C2—H2	1.0000	C14—H14	0.9500
C3—C4	1.506 (4)	C15—C16	1.392 (4)
C3—H3A	0.9900	C15—C18	1.511 (4)
C3—H3B	0.9900	C16—C17	1.387 (4)
C4—C5	1.386 (4)	C16—H16	0.9500
C4—C9	1.400 (4)	C17—H17	0.9500
C5—C6	1.393 (4)	C18—H18A	0.9800
C5—H5	0.9500	C18—H18B	0.9800
C6—C7	1.386 (4)	C18—H18C	0.9800
C6—H6	0.9500

N2—S1—N1	110.58 (11)	C9—C8—H8	120.8
N2—S1—C11	99.43 (12)	C7—C8—H8	120.8
N1—S1—C11	98.34 (11)	C8—C9—C4	121.5 (2)
O4—S2—O3	117.24 (12)	C8—C9—C10	129.0 (2)
O4—S2—N2	106.79 (12)	C4—C9—C10	109.5 (2)
O3—S2—N2	112.27 (11)	N1—C10—C9	113.4 (2)
O4—S2—C12	107.93 (11)	N1—C10—C2	100.5 (2)
O3—S2—C12	108.03 (12)	C9—C10—C2	103.0 (2)
N2—S2—C12	103.67 (12)	N1—C10—H10	113.0
C1—O1—C2	110.39 (19)	C9—C10—H10	113.0
C1—N1—C10	110.0 (2)	C2—C10—H10	113.0
C1—N1—S1	119.14 (18)	S1—C11—H11A	109.5
C10—N1—S1	129.59 (17)	S1—C11—H11B	109.5
S1—N2—S2	114.97 (13)	H11A—C11—H11B	109.5
O2—C1—O1	124.1 (2)	S1—C11—H11C	109.5
O2—C1—N1	127.5 (2)	H11A—C11—H11C	109.5
O1—C1—N1	108.5 (2)	H11B—C11—H11C	109.5
O1—C2—C3	110.0 (2)	C13—C12—C17	121.0 (2)
O1—C2—C10	102.1 (2)	C13—C12—S2	119.9 (2)
C3—C2—C10	106.1 (2)	C17—C12—S2	119.0 (2)
O1—C2—H2	112.7	C12—C13—C14	119.2 (2)
C3—C2—H2	112.7	C12—C13—H13	120.4
C10—C2—H2	112.7	C14—C13—H13	120.4
C4—C3—C2	103.5 (2)	C15—C14—C13	120.7 (3)
C4—C3—H3A	111.1	C15—C14—H14	119.6
C2—C3—H3A	111.1	C13—C14—H14	119.6
C4—C3—H3B	111.1	C14—C15—C16	118.9 (2)
C2—C3—H3B	111.1	C14—C15—C18	119.3 (3)
H3A—C3—H3B	109.0	C16—C15—C18	121.9 (3)
C5—C4—C9	120.2 (2)	C17—C16—C15	121.3 (2)
C5—C4—C3	128.9 (2)	C17—C16—H16	119.3
C9—C4—C3	110.8 (2)	C15—C16—H16	119.3
C4—C5—C6	118.1 (2)	C16—C17—C12	118.8 (2)
C4—C5—H5	120.9	C16—C17—H17	120.6
C6—C5—H5	120.9	C12—C17—H17	120.6
C7—C6—C5	121.6 (2)	C15—C18—H18A	109.5
C7—C6—H6	119.2	C15—C18—H18B	109.5
C5—C6—H6	119.2	H18A—C18—H18B	109.5
C6—C7—C8	120.1 (3)	C15—C18—H18C	109.5
C6—C7—H7	120.0	H18A—C18—H18C	109.5
C8—C7—H7	120.0	H18B—C18—H18C	109.5
C9—C8—C7	118.3 (2)

Selected geometric parameters (Å, º) top

S1—N2	1.594 (2)	S2—O3	1.451 (2)
S1—N1	1.692 (2)	S2—N2	1.631 (2)
S1—C11	1.782 (3)	S2—C12	1.768 (2)
S2—O4	1.4430 (19)

N2—S1—N1	110.58 (11)	O3—S2—N2	112.27 (11)
N2—S1—C11	99.43 (12)	O4—S2—C12	107.93 (11)
N1—S1—C11	98.34 (11)	O3—S2—C12	108.03 (12)
O4—S2—O3	117.24 (12)	N2—S2—C12	103.67 (12)
O4—S2—N2	106.79 (12)

Acknowledgements

GPS thanks Professor Joseph Marino at Notre Dame for financial support.

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