Crystal structure of 2,3-diphenyl-2,3-di­hydro-4H-1,3-benzo­thia­zin-4-one 1-oxide

Yennawar, H.P.; Fox, R.; Moyer, Q.J.; Yang, Z.; Silverberg, L.J.

doi:10.1107/S2056989017010313

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Volume 73| Part 8| August 2017| Pages 1189-1191

https://doi.org/10.1107/S2056989017010313

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Crystal structure of 2,3-diphenyl-2,3-dihydro-4H-1,3-benzothiazin-4-one 1-oxide

Hemant P. Yennawar,^a Ryan Fox,^b Quentin J. Moyer,^b Ziwei Yang ^b and Lee J. Silverberg ^b ^*

^aDepartment of Biochemistry and Molecular Biology, Pennsylvania State University, University Park, PA 16802, USA, and ^bPennsylvania State University, Schuylkill Campus, 200 University Drive, Schuylkill Haven, PA 17972, USA
^*Correspondence e-mail: ljs43@psu.edu

Edited by G. Smith, Queensland University of Technology, Australia (Received 17 June 2017; accepted 11 July 2017; online 17 July 2017)

In the racemic title compound, C₂₀H₁₅NO₂S, the planes of the two phenyl substituents form dihedral angles of 48.97 (15) and 69.26 (15)° with that of the fused benzene ring of the parent benzothiazine ring, while the heterocyclic thiazine ring exhibits a screw-boat pucker. The O atom on the S atom of the ring is pseudo-axial on the thiazine ring and trans to the 2-phenyl group. In the crystal, molecules are arranged in layers in the ac plane, the layers being linked across b through intermolecular C—H⋯O hydrogen-bonding interactions.

Keywords: crystal structure; benzothiazine; screw-boat pucker; S-oxide; 1,3-benzothiazin-4-one.

CCDC reference: 1561660

1. Chemical context

The 2,3-dihydro-4H-1,3-benzothiazin-4-one scaffold has shown a wide range of bioactivity, including antitumor (Li et al., 2012 ; Wang et al., 2015 ; Kamel et al., 2010 ; Nofal et al., 2014 ), antimicrobial (Popiolek et al., 2016 ; Mandour et al., 2007 ), antimalarial (Mei et al., 2013 ), HIV–RT inhibition (Jeng et al., 2015 ; Hou et al., 2016 ) and cyclooxygenase COX-2 enzyme inhibition (Zarghi et al., 2009 ). The S-oxides of these compounds have been little studied (a search found fewer than 50), despite the evidence of enhanced activity in the similar 2,3,5,6-tetrahydro-4H-1,3-thiazin-4-ones (Surrey et al., 1958 ; Surrey, 1963a ,b ) and 1,3-thiazolidin-4-ones (Gududuru et al., 2004 ). Also of potential interest is the triphenyltin chloride adduct, which may have enhanced antifungal activity (Eng et al., 1996 ).

Recently, we reported the crystal structures of 2,3-diphenyl-2,3,5,6-tetrahydro-4H-1,3-thiazine-4-one 1-oxide (Yennawar, Yang & Silverberg, 2016 ) and the 1:1 adduct of triphenyltin chloride and 2,3-diphenyl-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-one (Yennawar, Fox & Silverberg, 2016 ). Attempts to prepare the triphenyltin chloride adduct of 2,3-diphenyl-2,3-dihydro-4H-1,3-benzothiazin-4-one instead produced the sulfoxide 2,3-diphenyl-2,3-dihydro-4H-1,3-benzothiazin-4-one 1-oxide on two separate occasions. The sulfoxide was also intentionally prepared by oxidation of 2,3-diphenyl-2,3-dihydro-4H-1,3-benzothiazin-4-one with Oxone^®. It has not yet been determined how the sulfoxide formed in the tin reaction, but Bourgoin-Legay & Boudet (1969 ) have reported the air oxidation of 2-alkyl-4H-1,3-benzothiazines to give the sulfoxides, although the analogous 2-aryl compounds were less prone to air oxidation.

In this article, we report the crystal structure of the product from one of the reactions using tin, the title compound, namely 2,3-diphenyl-2,3-dihydro-4H-1,3-benzothiazin-4-one 1-oxide, (I). To the best of our knowledge, this is the first reported crystal structure of an S-oxide of a 2,3-dihydro-4H-1,3-benzothiazin-4-one.

2. Structural commentary

In the title racemic compound, the planes of the two phenyl substituents form dihedral angles of 48.97 (15) and 69.26 (15)° with that of the fused benzene ring of the parent benzothiazine system (Fig. 1). The O atom on the S atom is pseudo-axial and trans to the 2-phenyl ring, just as in 2,3-diphenyl-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-one 1-oxide (Yennawar, Yang & Silverberg, 2016). The thiazine ring has a screw-boat conformation, with a puckering amplitude of 0.686 (2) Å and θ = 65.6 (2)° (Cremer & Pople, 1975 ). The thiazine ring in 2,3-diphenyl-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-one 1-oxide (Yennawar, Yang & Silverberg, 2016) was in an envelope conformation. The overall molecular configuration is quite similar to the structure of 2,3-diphenyl-2,3-dihydro-4H-1,3-benzothiazin-4-one (Yennawar et al., 2014 ).

Figure 1
The molecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level.

3. Supramolecular features

The crystal lattice has layers of molecules comprising alternating enantiomers, extending along the a-axis direction and lying in the ac plane. The layers are linked across the b-cell direction through intermolecular C1—H⋯O2ⁱ hydrogen bonds (Fig. 2, Table 1) between molecules of the same chirality [symmetry code: (i) −x + $[{1\over 2}]$ , y − $[{3\over 2}]$ , −z + $[{1\over 2}]$ ]. While C—H⋯O interactions are also present in our two earlier structures (Yennawar et al., 2014; Yennawar, Yang & Silverberg, 2016), the differences in either the donor C or acceptor O atoms make them unique in each case. In the present structure, the chiral C atom donates the proton to the O atom at position 4 (⋯O—C) of the thiazine ring, while in our 2016 structure, the acceptor O atom was the one at position 1 (⋯O—S). In the 2014 structure, the two benzene-ring C atoms are the donors to the only O atom (⋯O—C) on the thiazine ring.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O2ⁱ	0.98	2.31	3.240 (3)	157
Symmetry code: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Figure 2
Crystal packing diagram showing C—H⋯O contacts as dotted red lines between molecules of (I)

which form chains along the b-axis direction.

4. Database survey

A literature search found no prior reports of a crystal structure of an S-oxide of a 2,3-dihydro-4H-1,3-benzothiazin-4-one. We have previously reported the crystal structures of 2,3-diphenyl-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-one 1-oxide (Yennawar, Yang & Silverberg, 2016) and 2,3-diphenyl-2,3-dihydro-4H-1,3-benzothiazin-4-one (Yennawar et al., 2014).

5. Synthesis and crystallization

A 2 ml reactivial with a stir bar was charged with 0.1004 g of 2,3-diphenyl-2,3-dihydro-4H-1,3-benzothiazin-4-one and 0.95 ml of acetone and stirred. The benzothiazinone did not fully dissolve. A 10 ml round-bottomed flask was charged with 0.1212 g of triphenyltin chloride and 2.0 ml of acetone and stirred. The contents of the 2 ml vial were added to the 10 ml flask and the vial was rinsed with an additional 0.5 ml of acetone, giving a clear solution, which was stirred for 2 h and then allowed to stand without stirring for 3 d. The solution was filtered through Celite and then concentrated under vacuum, giving a white solid. The solid was recrystallized from cyclohexane to give a yellow solid (yield 0.0755 g, 72%). Crystals suitable for X-ray analysis were obtained by slow evaporation from an acetone solution.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The H atoms were placed geometrically and allowed to ride on their parent C atoms during refinement, with C—H distances of 0.98 (methine) or 0.93 Å (aromatic) and with U_iso(H) = 1.2U_eq(C). Although of no particular significance in this racemic compound, the enantiomer chosen was the C1(S) one.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₀H₁₅NO₂S
M_r	333.39
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	9.1505 (16), 11.2712 (19), 16.379 (3)
β (°)	103.997 (6)
V (Å³)	1639.2 (5)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.21
Crystal size (mm)	0.20 × 0.16 × 0.14

Data collection
Diffractometer	Bruker CCD area detector
Absorption correction	Multi-scan (SADABS; Bruker, 2001 )
T_min, T_max	0.790, 0.9
No. of measured, independent and observed [I > 2σ(I)] reflections	12730, 4036, 3701
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.090, 0.231, 1.65
No. of reflections	4036
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.61, −0.34
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), olex2.solve (Bourhis et al., 2015 ), SHELXL97 (Sheldrick, 2008 ) and OLEX2 (Dolomanov et al., 2009 ).

Supporting information

CCDC reference: 1561660

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989017010313/zs2384sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989017010313/zs2384Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989017010313/zs2384Isup3.mol

Supporting information file. DOI: https://doi.org/10.1107/S2056989017010313/zs2384Isup4.cml

checkCIF report

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SMART (Bruker, 2001); program(s) used to solve structure: olex2.solve (Bourhis et al., 2015); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

rac-2,3-Diphenyl-2,3-dihydro-4H-1,3-benzothiazin-4-one 1-oxide top

Crystal data top

C₂₀H₁₅NO₂S	F(000) = 696
M_r = 333.39	D_x = 1.351 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.1505 (16) Å	Cell parameters from 975 reflections
b = 11.2712 (19) Å	θ = 2.9–28.1°
c = 16.379 (3) Å	µ = 0.21 mm⁻¹
β = 103.997 (6)°	T = 298 K
V = 1639.2 (5) Å³	Block, colorless
Z = 4	0.20 × 0.16 × 0.14 mm

Data collection top

Bruker CCD area detector diffractometer	4036 independent reflections
Radiation source: fine-focus sealed tube	3701 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
phi and ω scans	θ_max = 28.4°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −12→11
T_min = 0.790, T_max = 0.9	k = −14→14
12730 measured reflections	l = −21→21

Refinement top

Refinement on F²	Primary atom site location: iterative
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.090	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.231	H-atom parameters constrained
S = 1.65	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
4036 reflections	(Δ/σ)_max < 0.001
217 parameters	Δρ_max = 0.61 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Special details top

Experimental. The data collection nominally covered a full sphere of reciprocal space by a combination of 4 sets of ω scans each set at different φ and/or 2θ angles and each scan (10 s exposure) covering -0.300° degrees in ω. The crystal to detector distance was 5.82 cm.

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.

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 > 2sigma(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

	x	y	z	U_iso*/U_eq
C1	0.2072 (3)	0.6272 (2)	0.31199 (16)	0.0321 (5)
H1	0.1959	0.5611	0.2720	0.039*
C2	0.3510 (3)	0.8148 (2)	0.32892 (15)	0.0295 (5)
C3	0.3394 (3)	0.8157 (2)	0.41882 (15)	0.0303 (5)
C4	0.3293 (3)	0.7126 (2)	0.46419 (16)	0.0341 (6)
C5	0.3268 (3)	0.7173 (3)	0.54783 (18)	0.0473 (7)
H5	0.3222	0.6477	0.5776	0.057*
C6	0.3311 (4)	0.8261 (3)	0.58734 (19)	0.0516 (8)
H6	0.3298	0.8298	0.6439	0.062*
C7	0.3373 (3)	0.9288 (3)	0.54312 (18)	0.0467 (7)
H7	0.3384	1.0019	0.5696	0.056*
C8	0.3420 (3)	0.9239 (2)	0.45941 (17)	0.0384 (6)
H8	0.3470	0.9939	0.4301	0.046*
C9	0.0503 (3)	0.6611 (2)	0.31841 (15)	0.0339 (6)
C10	−0.0061 (3)	0.7748 (3)	0.30135 (18)	0.0434 (7)
H10	0.0541	0.8338	0.2868	0.052*
C11	−0.1521 (4)	0.8012 (3)	0.3059 (2)	0.0562 (9)
H11	−0.1896	0.8776	0.2938	0.067*
C12	−0.2407 (4)	0.7160 (4)	0.3280 (2)	0.0648 (10)
H12	−0.3379	0.7346	0.3316	0.078*
C13	−0.1875 (4)	0.6036 (4)	0.3447 (3)	0.0673 (10)
H13	−0.2485	0.5458	0.3599	0.081*
C14	−0.0414 (4)	0.5746 (3)	0.3393 (2)	0.0526 (8)
H14	−0.0061	0.4974	0.3498	0.063*
C15	0.3197 (3)	0.7045 (2)	0.19894 (16)	0.0320 (5)
C16	0.2398 (4)	0.7703 (3)	0.13225 (17)	0.0446 (7)
H16	0.1642	0.8216	0.1393	0.053*
C17	0.2729 (5)	0.7592 (3)	0.05491 (19)	0.0574 (9)
H17	0.2198	0.8038	0.0096	0.069*
C18	0.3845 (4)	0.6825 (3)	0.0442 (2)	0.0582 (9)
H18	0.4082	0.6770	−0.0077	0.070*
C19	0.4602 (4)	0.6144 (3)	0.1105 (2)	0.0548 (8)
H19	0.5333	0.5610	0.1030	0.066*
C20	0.4279 (3)	0.6249 (3)	0.18879 (18)	0.0430 (7)
H20	0.4787	0.5787	0.2338	0.052*
N1	0.2910 (2)	0.71883 (18)	0.28149 (13)	0.0304 (5)
O1	0.4735 (2)	0.5462 (2)	0.39909 (15)	0.0535 (6)
O2	0.4139 (2)	0.89553 (17)	0.30137 (12)	0.0421 (5)
S1	0.32220 (8)	0.57148 (6)	0.41423 (4)	0.0392 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0354 (12)	0.0251 (11)	0.0372 (13)	−0.0058 (9)	0.0112 (10)	−0.0019 (10)
C2	0.0296 (11)	0.0270 (11)	0.0303 (12)	0.0005 (9)	0.0041 (9)	0.0034 (9)
C3	0.0273 (11)	0.0307 (12)	0.0309 (13)	−0.0032 (9)	0.0032 (9)	0.0014 (9)
C4	0.0332 (12)	0.0328 (12)	0.0351 (13)	0.0028 (10)	0.0059 (10)	0.0033 (10)
C5	0.0507 (16)	0.0536 (17)	0.0366 (15)	0.0039 (13)	0.0087 (12)	0.0134 (13)
C6	0.0555 (18)	0.068 (2)	0.0303 (14)	0.0079 (15)	0.0083 (13)	−0.0011 (14)
C7	0.0493 (16)	0.0513 (17)	0.0372 (15)	0.0007 (13)	0.0062 (12)	−0.0131 (13)
C8	0.0415 (14)	0.0347 (14)	0.0370 (14)	−0.0045 (10)	0.0058 (11)	−0.0013 (11)
C9	0.0342 (12)	0.0395 (14)	0.0284 (12)	−0.0097 (10)	0.0079 (10)	−0.0089 (10)
C10	0.0387 (14)	0.0467 (15)	0.0431 (15)	0.0005 (12)	0.0065 (12)	−0.0077 (13)
C11	0.0443 (17)	0.070 (2)	0.0495 (18)	0.0094 (15)	0.0029 (14)	−0.0180 (16)
C12	0.0364 (15)	0.101 (3)	0.058 (2)	−0.0051 (18)	0.0132 (14)	−0.032 (2)
C13	0.0468 (18)	0.089 (3)	0.072 (2)	−0.0270 (19)	0.0265 (17)	−0.011 (2)
C14	0.0475 (16)	0.0529 (19)	0.0606 (19)	−0.0145 (14)	0.0196 (15)	−0.0049 (15)
C15	0.0343 (12)	0.0315 (12)	0.0312 (12)	−0.0057 (9)	0.0101 (10)	−0.0017 (10)
C16	0.0587 (18)	0.0383 (14)	0.0378 (15)	0.0025 (12)	0.0136 (13)	0.0016 (12)
C17	0.085 (2)	0.0500 (18)	0.0366 (16)	−0.0038 (17)	0.0139 (15)	0.0080 (14)
C18	0.078 (2)	0.063 (2)	0.0414 (17)	−0.0122 (17)	0.0293 (17)	−0.0071 (15)
C19	0.0516 (18)	0.065 (2)	0.0541 (19)	0.0021 (15)	0.0252 (15)	−0.0110 (16)
C20	0.0379 (14)	0.0530 (17)	0.0380 (15)	0.0047 (12)	0.0089 (11)	−0.0052 (12)
N1	0.0350 (10)	0.0270 (10)	0.0305 (10)	−0.0046 (8)	0.0106 (8)	−0.0016 (8)
O1	0.0475 (12)	0.0473 (12)	0.0673 (14)	0.0153 (9)	0.0169 (10)	0.0093 (10)
O2	0.0545 (12)	0.0346 (10)	0.0385 (10)	−0.0164 (8)	0.0139 (9)	0.0009 (8)
S1	0.0453 (4)	0.0278 (4)	0.0463 (4)	0.0023 (2)	0.0145 (3)	0.0098 (3)

Geometric parameters (Å, º) top

C1—H1	0.9800	C10—C11	1.388 (4)
C1—C9	1.514 (3)	C11—H11	0.9300
C1—N1	1.446 (3)	C11—C12	1.361 (5)
C1—S1	1.858 (3)	C12—H12	0.9300
C2—C3	1.502 (3)	C12—C13	1.361 (6)
C2—N1	1.367 (3)	C13—H13	0.9300
C2—O2	1.220 (3)	C13—C14	1.400 (5)
C3—C4	1.394 (3)	C14—H14	0.9300
C3—C8	1.386 (3)	C15—C16	1.375 (4)
C4—C5	1.377 (4)	C15—C20	1.375 (4)
C4—S1	1.783 (3)	C15—N1	1.447 (3)
C5—H5	0.9300	C16—H16	0.9300
C5—C6	1.383 (4)	C16—C17	1.378 (4)
C6—H6	0.9300	C17—H17	0.9300
C6—C7	1.374 (4)	C17—C18	1.381 (5)
C7—H7	0.9300	C18—H18	0.9300
C7—C8	1.383 (4)	C18—C19	1.373 (5)
C8—H8	0.9300	C19—H19	0.9300
C9—C10	1.384 (4)	C19—C20	1.389 (4)
C9—C14	1.383 (4)	C20—H20	0.9300
C10—H10	0.9300	O1—S1	1.491 (2)

C9—C1—H1	106.9	C12—C11—H11	119.8
C9—C1—S1	111.28 (17)	C11—C12—H12	119.9
N1—C1—H1	106.9	C13—C12—C11	120.2 (3)
N1—C1—C9	115.8 (2)	C13—C12—H12	119.9
N1—C1—S1	108.68 (16)	C12—C13—H13	119.8
S1—C1—H1	106.9	C12—C13—C14	120.4 (3)
N1—C2—C3	116.7 (2)	C14—C13—H13	119.8
O2—C2—C3	120.6 (2)	C9—C14—C13	119.8 (3)
O2—C2—N1	122.7 (2)	C9—C14—H14	120.1
C4—C3—C2	123.1 (2)	C13—C14—H14	120.1
C8—C3—C2	118.6 (2)	C16—C15—N1	120.0 (2)
C8—C3—C4	118.3 (2)	C20—C15—C16	121.0 (3)
C3—C4—S1	119.9 (2)	C20—C15—N1	119.0 (2)
C5—C4—C3	121.2 (2)	C15—C16—H16	120.4
C5—C4—S1	118.9 (2)	C15—C16—C17	119.2 (3)
C4—C5—H5	120.2	C17—C16—H16	120.4
C4—C5—C6	119.6 (3)	C16—C17—H17	119.8
C6—C5—H5	120.2	C16—C17—C18	120.5 (3)
C5—C6—H6	120.0	C18—C17—H17	119.8
C7—C6—C5	120.0 (3)	C17—C18—H18	120.1
C7—C6—H6	120.0	C19—C18—C17	119.8 (3)
C6—C7—H7	119.9	C19—C18—H18	120.1
C6—C7—C8	120.3 (3)	C18—C19—H19	119.9
C8—C7—H7	119.9	C18—C19—C20	120.2 (3)
C3—C8—H8	119.7	C20—C19—H19	119.9
C7—C8—C3	120.6 (2)	C15—C20—C19	119.2 (3)
C7—C8—H8	119.7	C15—C20—H20	120.4
C10—C9—C1	122.2 (2)	C19—C20—H20	120.4
C14—C9—C1	118.8 (3)	C1—N1—C15	118.32 (19)
C14—C9—C10	119.0 (3)	C2—N1—C1	122.9 (2)
C9—C10—H10	119.9	C2—N1—C15	118.7 (2)
C9—C10—C11	120.3 (3)	C4—S1—C1	93.56 (11)
C11—C10—H10	119.9	O1—S1—C1	105.12 (12)
C10—C11—H11	119.8	O1—S1—C4	108.31 (13)
C12—C11—C10	120.4 (3)

C1—C9—C10—C11	178.3 (2)	C15—C16—C17—C18	0.4 (5)
C1—C9—C14—C13	−179.3 (3)	C16—C15—C20—C19	2.4 (4)
C2—C3—C4—C5	176.6 (2)	C16—C15—N1—C1	105.0 (3)
C2—C3—C4—S1	−2.5 (3)	C16—C15—N1—C2	−78.4 (3)
C2—C3—C8—C7	−177.6 (2)	C16—C17—C18—C19	1.7 (5)
C3—C2—N1—C1	5.9 (3)	C17—C18—C19—C20	−1.9 (5)
C3—C2—N1—C15	−170.5 (2)	C18—C19—C20—C15	−0.2 (5)
C3—C4—C5—C6	1.3 (4)	C20—C15—C16—C17	−2.5 (4)
C3—C4—S1—C1	−36.3 (2)	C20—C15—N1—C1	−75.2 (3)
C3—C4—S1—O1	70.9 (2)	C20—C15—N1—C2	101.3 (3)
C4—C3—C8—C7	1.1 (4)	N1—C1—C9—C10	−4.0 (3)
C4—C5—C6—C7	0.3 (5)	N1—C1—C9—C14	173.9 (2)
C5—C4—S1—C1	144.5 (2)	N1—C1—S1—C4	60.72 (18)
C5—C4—S1—O1	−108.3 (2)	N1—C1—S1—O1	−49.3 (2)
C5—C6—C7—C8	−1.2 (5)	N1—C2—C3—C4	26.3 (3)
C6—C7—C8—C3	0.5 (4)	N1—C2—C3—C8	−155.1 (2)
C8—C3—C4—C5	−2.0 (4)	N1—C15—C16—C17	177.3 (3)
C8—C3—C4—S1	178.89 (19)	N1—C15—C20—C19	−177.4 (2)
C9—C1—N1—C2	73.2 (3)	O2—C2—C3—C4	−152.3 (3)
C9—C1—N1—C15	−110.4 (2)	O2—C2—C3—C8	26.3 (3)
C9—C1—S1—C4	−67.89 (18)	O2—C2—N1—C1	−175.5 (2)
C9—C1—S1—O1	−177.94 (17)	O2—C2—N1—C15	8.1 (4)
C9—C10—C11—C12	0.7 (4)	S1—C1—C9—C10	120.8 (2)
C10—C9—C14—C13	−1.4 (4)	S1—C1—C9—C14	−61.4 (3)
C10—C11—C12—C13	−0.8 (5)	S1—C1—N1—C2	−52.8 (3)
C11—C12—C13—C14	−0.1 (6)	S1—C1—N1—C15	123.56 (19)
C12—C13—C14—C9	1.3 (5)	S1—C4—C5—C6	−179.5 (2)
C14—C9—C10—C11	0.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O2ⁱ	0.98	2.31	3.240 (3)	157

Symmetry code: (i) −x+1/2, y−1/2, −z+1/2.

Funding information

Funding for this research was provided by: Penn State Schuylkill; National Science Foundation (grant No. CHEM-0131112) for the X-ray diffractometer.

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