(±)-3-Benz­yloxy-1-(4-meth­oxy­benz­yl)piperidine-2-thione

Pienaar, D.P.; Khorasani, S.; de Koning, C.B.; Michael, J.P.

doi:10.1107/S1600536812048854

organic compounds

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ISSN: 2056-9890

Volume 69| Part 1| January 2013| Page o21

https://doi.org/10.1107/S1600536812048854

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(±)-3-Benzyloxy-1-(4-methoxybenzyl)piperidine-2-thione

Daniel P. Pienaar,^a Sanaz Khorasani,^a Charles B. de Koning ^a and Joseph P. Michael ^a ^*

^aMolecular Sciences Institute, School of Chemistry, University of the Witwatersrand, PO Wits 2050, Johannesburg, South Africa
^*Correspondence e-mail: joseph.michael@wits.ac.za

(Received 26 November 2012; accepted 28 November 2012; online 5 December 2012)

The title molecule, C₂₀H₂₃NO₂S, adopts a twisted conformation in which the two aromatic rings connected to the central piperidine ring are orientated trans to each other. An intramolecular C—H⋯S contact occurs. In the crystal, C—H⋯π and C—H⋯O interactions act to stabilize the structure in three dimensions.

Related literature

For the use of related piperidinethiones in the synthesis of febrifugine analogues, see: Michael et al. (2006 ). For information on the biological activity of febrifugine, see: Murata et al. (1998 ).

Experimental

Crystal data

C₂₀H₂₃NO₂S
M_r = 341.45
Orthorhombic, P b c a
a = 18.371 (3) Å
b = 10.4844 (15) Å
c = 18.467 (3) Å
V = 3556.9 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 173 K
0.47 × 0.28 × 0.05 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
22717 measured reflections
4286 independent reflections
2949 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.098
S = 1.01
4286 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C16–C21 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯S1	0.99	2.54	3.0760 (16)	114
C13—H13⋯O2ⁱ	0.95	2.59	3.4913 (19)	158
C6—H6B⋯Cg1ⁱ	0.99	2.54	3.5066 (19)	165
C14—H14A⋯Cg1ⁱⁱ	0.98	2.61	3.455 (2)	144
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) -x, -y, -z+1.

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT-NT (Bruker, 2005); data reduction: SAINT-NT; 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 SCHAKAL99 (Keller, 1999 ); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812048854/go2079sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812048854/go2079Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812048854/go2079Isup3.cml

checkCIF report

Comment top

The title piperidinethione was prepared as an intermediate for the total synthesis of febrifugine, a quinazoline alkaloid with potent antimalarial activity (Murata et al., 1998). Related thiolactam intermediates have been used in the synthesis of febrifugine analogues in ongoing investigations in our laboratories (Michael et al., 2006). It should be noted that, although an optically pure lactam was used in the synthesis of the title compound, racemization took place during the replacement of oxygen by sulfur with Lawesson's reagent.

The title organic compound (Fig. 1) crystallizes in the space group Pbca. The molecule adopts a twisted conformation in which the two aromatic rings connected to the piperidine ring are orientated trans to each other. The aromatic rings are also rotated with respect to each other such that the angle between least squares planes defined by the two rings is 59.04 (6)°. The most significant weak interactions in this structure are listed in Table 1. Two C—H···π interactions involving the ring defined by C16—C21 are present in the structure while no such interactions exist for the aromatic ring defined by C8—C13. These two C—H···π interactions act to bring three molecules together which interact further through the C—H···O interaction as shown in Fig. 2. No significant π···π interactions are present in the structure.

Related literature top

For the use of related piperidinethiones in the synthesis of febrifugine analogues, see: Michael et al. (2006). For information on the biological activity of febrifugine, see: Murata et al. (1998).

Experimental top

The title compound was synthesized by heating a mixture of (3S)-3-benzyloxy-1-(4-methoxybenzyl)piperidin-2-one (170 mg, 0.52 mmol) and Lawesson's reagent (106 mg, 0.26 mmol) in benzene (8 ml) under reflux for 4 h. After evaporation of the solvent in vacuo, the residue was purified by column chromatography on silica gel with hexane/ethyl acetate (4:1 v/v) as eluent to yield the racemic product as shiny colourless plates (174 mg, 98%), m.p. 349.5–351.5 K.

Structure description top

For the use of related piperidinethiones in the synthesis of febrifugine analogues, see: Michael et al. (2006). For information on the biological activity of febrifugine, see: Murata et al. (1998).

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 SCHAKAL99 (Keller, 1999); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of (I), showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. C—H···π and C—H···O interactions in the structure of (I). Only the aromatic ring defined by C16—C21 is involved in C—H···π interactions but these act to bring three molecules together.

(±)-3-Benzyloxy-1-(4-methoxybenzyl)piperidine-2-thione top

Crystal data top

C₂₀H₂₃NO₂S	F(000) = 1456
M_r = 341.45	D_x = 1.275 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 978 reflections
a = 18.371 (3) Å	θ = 2.5–28.0°
b = 10.4844 (15) Å	µ = 0.19 mm⁻¹
c = 18.467 (3) Å	T = 173 K
V = 3556.9 (9) Å³	Plate, colourless
Z = 8	0.47 × 0.28 × 0.05 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	2949 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.046
Graphite monochromator	θ_max = 28.0°, θ_min = 2.2°
phi and ω scans	h = −24→19
22717 measured reflections	k = −13→13
4286 independent reflections	l = −23→24

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.098	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0464P)² + 0.5277P] where P = (F_o² + 2F_c²)/3
4286 reflections	(Δ/σ)_max = 0.003
218 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₂₀H₂₃NO₂S	V = 3556.9 (9) Å³
M_r = 341.45	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 18.371 (3) Å	µ = 0.19 mm⁻¹
b = 10.4844 (15) Å	T = 173 K
c = 18.467 (3) Å	0.47 × 0.28 × 0.05 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	2949 reflections with I > 2σ(I)
22717 measured reflections	R_int = 0.046
4286 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.098	H-atom parameters constrained
S = 1.01	Δρ_max = 0.26 e Å⁻³
4286 reflections	Δρ_min = −0.26 e Å⁻³
218 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.

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

	x	y	z	U_iso*/U_eq
C2	−0.00224 (8)	0.06796 (14)	0.61154 (8)	0.0260 (3)
C3	0.02325 (8)	0.19576 (13)	0.58013 (8)	0.0278 (3)
H3	0.0100	0.1991	0.5277	0.033*
C4	0.10388 (8)	0.21947 (16)	0.58763 (9)	0.0339 (4)
H4A	0.1153	0.3082	0.5733	0.041*
H4B	0.1311	0.1611	0.5553	0.041*
C5	0.12655 (9)	0.19740 (15)	0.66565 (9)	0.0371 (4)
H5A	0.1790	0.2166	0.6715	0.045*
H5B	0.0988	0.2548	0.6980	0.045*
C6	0.11198 (8)	0.06000 (15)	0.68586 (9)	0.0339 (4)
H6A	0.1511	0.0060	0.6654	0.041*
H6B	0.1140	0.0518	0.7392	0.041*
C7	0.02107 (8)	−0.11296 (14)	0.69241 (8)	0.0310 (3)
H7A	−0.0293	−0.1356	0.6782	0.037*
H7B	0.0225	−0.1057	0.7458	0.037*
C8	0.07247 (8)	−0.21843 (14)	0.66849 (8)	0.0265 (3)
C9	0.09864 (8)	−0.22570 (14)	0.59808 (8)	0.0293 (3)
H9	0.0846	−0.1624	0.5640	0.035*
C10	0.14501 (8)	−0.32359 (14)	0.57614 (8)	0.0295 (3)
H10	0.1621	−0.3273	0.5276	0.035*
C11	0.16592 (8)	−0.41589 (14)	0.62622 (9)	0.0311 (3)
C12	0.13904 (9)	−0.41094 (14)	0.69669 (9)	0.0353 (4)
H12	0.1522	−0.4751	0.7306	0.042*
C13	0.09325 (9)	−0.31299 (14)	0.71751 (9)	0.0324 (4)
H13	0.0757	−0.3100	0.7659	0.039*
C14	0.23736 (9)	−0.52714 (17)	0.53823 (10)	0.0434 (4)
H14A	0.1953	−0.5379	0.5061	0.065*
H14B	0.2693	−0.6017	0.5342	0.065*
H14C	0.2643	−0.4503	0.5243	0.065*
C15	−0.02311 (8)	0.40960 (13)	0.58316 (9)	0.0293 (3)
H15A	−0.0249	0.3973	0.5300	0.035*
H15B	0.0205	0.4611	0.5948	0.035*
C16	−0.09058 (8)	0.47794 (13)	0.60827 (8)	0.0256 (3)
C17	−0.15243 (8)	0.41094 (14)	0.62983 (8)	0.0300 (3)
H17	−0.1518	0.3203	0.6303	0.036*
C18	−0.21487 (9)	0.47569 (15)	0.65056 (9)	0.0359 (4)
H18	−0.2567	0.4292	0.6654	0.043*
C19	−0.21667 (9)	0.60777 (16)	0.64975 (9)	0.0373 (4)
H19	−0.2596	0.6518	0.6640	0.045*
C20	−0.15566 (9)	0.67528 (15)	0.62815 (9)	0.0351 (4)
H20	−0.1569	0.7658	0.6270	0.042*
C21	−0.09291 (8)	0.61116 (14)	0.60820 (8)	0.0303 (3)
H21	−0.0510	0.6582	0.5943	0.036*
N1	0.04038 (6)	0.01121 (11)	0.66005 (6)	0.0267 (3)
S1	−0.08302 (2)	0.01240 (4)	0.58307 (2)	0.03658 (12)
O1	0.21278 (6)	−0.51478 (10)	0.61136 (7)	0.0413 (3)
O2	−0.01884 (6)	0.28903 (9)	0.61845 (5)	0.0299 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C2	0.0271 (8)	0.0236 (7)	0.0273 (8)	0.0015 (6)	0.0041 (6)	−0.0019 (6)
C3	0.0297 (8)	0.0245 (7)	0.0293 (8)	0.0041 (6)	0.0051 (6)	0.0001 (6)
C4	0.0289 (8)	0.0281 (8)	0.0447 (10)	0.0004 (6)	0.0072 (7)	0.0032 (7)
C5	0.0297 (9)	0.0303 (9)	0.0514 (10)	−0.0019 (7)	−0.0028 (7)	−0.0028 (7)
C6	0.0296 (8)	0.0319 (8)	0.0402 (9)	−0.0004 (7)	−0.0079 (7)	−0.0001 (7)
C7	0.0320 (8)	0.0288 (8)	0.0321 (8)	0.0011 (6)	0.0032 (7)	0.0063 (6)
C8	0.0274 (8)	0.0219 (7)	0.0303 (8)	−0.0025 (6)	−0.0027 (6)	0.0021 (6)
C9	0.0318 (8)	0.0239 (7)	0.0322 (8)	−0.0015 (6)	−0.0036 (6)	0.0049 (6)
C10	0.0311 (8)	0.0270 (8)	0.0303 (8)	−0.0038 (6)	−0.0010 (6)	−0.0019 (6)
C11	0.0304 (8)	0.0228 (8)	0.0402 (9)	0.0001 (6)	−0.0102 (7)	−0.0045 (6)
C12	0.0468 (10)	0.0243 (8)	0.0348 (9)	0.0027 (7)	−0.0128 (7)	0.0044 (7)
C13	0.0413 (9)	0.0277 (8)	0.0282 (8)	−0.0028 (7)	−0.0036 (7)	0.0030 (6)
C14	0.0348 (9)	0.0402 (10)	0.0552 (11)	0.0066 (7)	−0.0036 (8)	−0.0135 (8)
C15	0.0287 (8)	0.0220 (7)	0.0371 (9)	0.0003 (6)	0.0033 (6)	0.0049 (6)
C16	0.0258 (7)	0.0222 (7)	0.0290 (7)	−0.0001 (6)	−0.0030 (6)	0.0012 (6)
C17	0.0298 (8)	0.0212 (7)	0.0390 (9)	−0.0024 (6)	−0.0011 (6)	0.0005 (6)
C18	0.0261 (8)	0.0327 (9)	0.0488 (10)	−0.0036 (7)	0.0016 (7)	0.0014 (7)
C19	0.0308 (9)	0.0337 (9)	0.0473 (10)	0.0083 (7)	0.0001 (7)	−0.0015 (7)
C20	0.0404 (10)	0.0209 (8)	0.0440 (10)	0.0037 (7)	−0.0011 (7)	−0.0001 (7)
C21	0.0314 (8)	0.0239 (8)	0.0356 (8)	−0.0043 (6)	0.0001 (6)	0.0024 (6)
N1	0.0265 (6)	0.0233 (6)	0.0303 (7)	0.0009 (5)	0.0005 (5)	0.0009 (5)
S1	0.0307 (2)	0.0367 (2)	0.0423 (2)	−0.00675 (17)	−0.00588 (17)	0.00665 (18)
O1	0.0433 (7)	0.0328 (6)	0.0479 (7)	0.0116 (5)	−0.0118 (5)	−0.0078 (5)
O2	0.0343 (6)	0.0235 (5)	0.0318 (6)	0.0065 (4)	0.0075 (5)	0.0037 (4)

Geometric parameters (Å, º) top

C2—N1	1.3302 (19)	C11—O1	1.3752 (19)
C2—C3	1.533 (2)	C11—C12	1.393 (2)
C2—S1	1.6788 (15)	C12—C13	1.382 (2)
C3—O2	1.4334 (17)	C12—H12	0.9500
C3—C4	1.509 (2)	C13—H13	0.9500
C3—H3	1.0000	C14—O1	1.430 (2)
C4—C5	1.518 (2)	C14—H14A	0.9800
C4—H4A	0.9900	C14—H14B	0.9800
C4—H4B	0.9900	C14—H14C	0.9800
C5—C6	1.512 (2)	C15—O2	1.4244 (17)
C5—H5A	0.9900	C15—C16	1.505 (2)
C5—H5B	0.9900	C15—H15A	0.9900
C6—N1	1.4897 (19)	C15—H15B	0.9900
C6—H6A	0.9900	C16—C17	1.394 (2)
C6—H6B	0.9900	C16—C21	1.397 (2)
C7—N1	1.4756 (18)	C17—C18	1.387 (2)
C7—C8	1.520 (2)	C17—H17	0.9500
C7—H7A	0.9900	C18—C19	1.385 (2)
C7—H7B	0.9900	C18—H18	0.9500
C8—C9	1.388 (2)	C19—C20	1.384 (2)
C8—C13	1.396 (2)	C19—H19	0.9500
C9—C10	1.394 (2)	C20—C21	1.384 (2)
C9—H9	0.9500	C20—H20	0.9500
C10—C11	1.393 (2)	C21—H21	0.9500
C10—H10	0.9500

N1—C2—C3	117.77 (13)	O1—C11—C10	124.33 (15)
N1—C2—S1	125.17 (12)	C12—C11—C10	119.78 (14)
C3—C2—S1	117.04 (11)	C13—C12—C11	120.22 (14)
O2—C3—C4	111.83 (12)	C13—C12—H12	119.9
O2—C3—C2	104.16 (11)	C11—C12—H12	119.9
C4—C3—C2	114.15 (12)	C12—C13—C8	120.93 (15)
O2—C3—H3	108.8	C12—C13—H13	119.5
C4—C3—H3	108.8	C8—C13—H13	119.5
C2—C3—H3	108.8	O1—C14—H14A	109.5
C3—C4—C5	109.36 (13)	O1—C14—H14B	109.5
C3—C4—H4A	109.8	H14A—C14—H14B	109.5
C5—C4—H4A	109.8	O1—C14—H14C	109.5
C3—C4—H4B	109.8	H14A—C14—H14C	109.5
C5—C4—H4B	109.8	H14B—C14—H14C	109.5
H4A—C4—H4B	108.3	O2—C15—C16	109.08 (12)
C6—C5—C4	109.33 (13)	O2—C15—H15A	109.9
C6—C5—H5A	109.8	C16—C15—H15A	109.9
C4—C5—H5A	109.8	O2—C15—H15B	109.9
C6—C5—H5B	109.8	C16—C15—H15B	109.9
C4—C5—H5B	109.8	H15A—C15—H15B	108.3
H5A—C5—H5B	108.3	C17—C16—C21	118.62 (14)
N1—C6—C5	113.86 (13)	C17—C16—C15	121.30 (13)
N1—C6—H6A	108.8	C21—C16—C15	120.05 (13)
C5—C6—H6A	108.8	C18—C17—C16	120.43 (14)
N1—C6—H6B	108.8	C18—C17—H17	119.8
C5—C6—H6B	108.8	C16—C17—H17	119.8
H6A—C6—H6B	107.7	C19—C18—C17	120.40 (15)
N1—C7—C8	112.02 (12)	C19—C18—H18	119.8
N1—C7—H7A	109.2	C17—C18—H18	119.8
C8—C7—H7A	109.2	C20—C19—C18	119.67 (15)
N1—C7—H7B	109.2	C20—C19—H19	120.2
C8—C7—H7B	109.2	C18—C19—H19	120.2
H7A—C7—H7B	107.9	C19—C20—C21	120.17 (15)
C9—C8—C13	118.27 (14)	C19—C20—H20	119.9
C9—C8—C7	121.82 (13)	C21—C20—H20	119.9
C13—C8—C7	119.89 (13)	C20—C21—C16	120.71 (14)
C8—C9—C10	121.62 (14)	C20—C21—H21	119.6
C8—C9—H9	119.2	C16—C21—H21	119.6
C10—C9—H9	119.2	C2—N1—C7	121.73 (13)
C11—C10—C9	119.16 (14)	C2—N1—C6	125.56 (13)
C11—C10—H10	120.4	C7—N1—C6	112.68 (12)
C9—C10—H10	120.4	C11—O1—C14	117.04 (13)
O1—C11—C12	115.88 (14)	C15—O2—C3	114.16 (11)

N1—C2—C3—O2	−101.85 (14)	C21—C16—C17—C18	0.2 (2)
S1—C2—C3—O2	76.83 (14)	C15—C16—C17—C18	−177.91 (15)
N1—C2—C3—C4	20.40 (19)	C16—C17—C18—C19	0.3 (2)
S1—C2—C3—C4	−160.92 (11)	C17—C18—C19—C20	−0.1 (3)
O2—C3—C4—C5	67.16 (16)	C18—C19—C20—C21	−0.7 (3)
C2—C3—C4—C5	−50.78 (17)	C19—C20—C21—C16	1.2 (2)
C3—C4—C5—C6	62.00 (17)	C17—C16—C21—C20	−0.9 (2)
C4—C5—C6—N1	−43.34 (18)	C15—C16—C21—C20	177.18 (14)
N1—C7—C8—C9	−39.1 (2)	C3—C2—N1—C7	−178.97 (12)
N1—C7—C8—C13	142.40 (14)	S1—C2—N1—C7	2.5 (2)
C13—C8—C9—C10	−0.6 (2)	C3—C2—N1—C6	−1.2 (2)
C7—C8—C9—C10	−179.13 (14)	S1—C2—N1—C6	−179.75 (12)
C8—C9—C10—C11	−0.4 (2)	C8—C7—N1—C2	112.23 (15)
C9—C10—C11—O1	−178.26 (14)	C8—C7—N1—C6	−65.82 (16)
C9—C10—C11—C12	1.5 (2)	C5—C6—N1—C2	13.5 (2)
O1—C11—C12—C13	178.11 (14)	C5—C6—N1—C7	−168.55 (13)
C10—C11—C12—C13	−1.7 (2)	C12—C11—O1—C14	175.93 (13)
C11—C12—C13—C8	0.7 (2)	C10—C11—O1—C14	−4.3 (2)
C9—C8—C13—C12	0.4 (2)	C16—C15—O2—C3	155.93 (12)
C7—C8—C13—C12	179.00 (14)	C4—C3—O2—C15	76.17 (15)
O2—C15—C16—C17	−29.49 (19)	C2—C3—O2—C15	−160.07 (12)
O2—C15—C16—C21	152.48 (13)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C16–C21 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···S1	0.99	2.54	3.0760 (16)	114
C13—H13···O2ⁱ	0.95	2.59	3.4913 (19)	158
C6—H6B···Cg1ⁱ	0.99	2.54	3.5066 (19)	165
C14—H14A···Cg1ⁱⁱ	0.98	2.61	3.455 (2)	144

Symmetry codes: (i) −x, y−1/2, −z+3/2; (ii) −x, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₃NO₂S
M_r	341.45
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	173
a, b, c (Å)	18.371 (3), 10.4844 (15), 18.467 (3)
V (Å³)	3556.9 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.47 × 0.28 × 0.05

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	22717, 4286, 2949
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.098, 1.01
No. of reflections	4286
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.26

Computer programs: APEX2 (Bruker, 2005), SAINT-NT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and SCHAKAL99 (Keller, 1999), WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C16–C21 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···S1	0.99	2.54	3.0760 (16)	114
C13—H13···O2ⁱ	0.95	2.59	3.4913 (19)	158
C6—H6B···Cg1ⁱ	0.99	2.54	3.5066 (19)	165
C14—H14A···Cg1ⁱⁱ	0.98	2.61	3.455 (2)	144

Symmetry codes: (i) −x, y−1/2, −z+3/2; (ii) −x, −y, −z+1.

Acknowledgements

This work was supported by the University of the Witwatersrand and the National Research Foundation, Pretoria (grant number 78837).

References

Bruker (2005). APEX2 and SAINT-NT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Keller, E. (1999). SCHAKAL99. University of Freiberg, Germany. Google Scholar
Michael, J. P., de Koning, C. B. & Pienaar, D. P. (2006). Synlett, pp. 383–386. Web of Science CrossRef Google Scholar
Murata, K., Takano, F., Fushiya, S. & Oshima, Y. (1998). J. Nat. Prod. 61, 729–733. Web of Science CrossRef CAS PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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