(1R,3S,5R,6S)-6-Acet­oxy-3-(4-methyl­phenyl­sulfon­yloxy)tropane

Yang, L.-M.; Zhu, L.; Niu, Y.-Y.; Chen, H.-Z.; Lu, Y.

doi:10.1107/S1600536808035800

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2331

doi:10.1107/S1600536808035800

Open

access

(1R,3S,5R,6S)-6-Acetoxy-3-(4-methylphenylsulfonyloxy)tropane

Li-Min Yang,^a ^* Liang Zhu,^a Yin-Yao Niu,^a Hong-Zhuan Chen ^a and Yang Lu ^a

^aDepartment of Pharmacy, Shanghai Jiao Tong University School of Medicine, South Chongqing Road 280, Shanghai 200025, People's Republic of China
^*Correspondence e-mail: huaxue@shsmu.edu.cn

(Received 29 October 2008; accepted 31 October 2008; online 13 November 2008)

In the title compound [systematic name: (1R,3S,5R,6S)-8-methyl-3-(4-methylphenylsulfonyloxy)-8-azabicyclo[3.2.1]octan-6-yl acetate], C₁₇H₂₃NO₅S, the fused piperidine ring exists in a chair conformation with the N atom and one C atom displaced by 0.876 (2) and −0.460 (3) Å, respectively, on opposite sides of the mean plane defined by the other four atoms. The fused pyrrolidine ring adopts an envelope conformation with the N atom deviating by 0.644 (3) Å from the mean plane of the other four atoms.

Related literature

For the synthesis, see: Yang & Wang (1998 ); Xie et al. (2005 ). For the pharmacological activity, see: Zhu et al. (2008 ).

Experimental

Crystal data

C₁₇H₂₃NO₅S
M_r = 353.42
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.9241 (6) Å
b = 15.5069 (14) Å
c = 16.1020 (15) Å
V = 1728.9 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 293 (2) K
0.47 × 0.41 × 0.31 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ) T_min = 0.751, T_max = 1.000 (expected range = 0.702–0.935)
10216 measured reflections
3770 independent reflections
3238 reflections with I > 2σ(I)
R_int = 0.066

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.093
S = 0.97
3770 reflections
221 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.23 e Å⁻³
Absolute structure: Flack (1983 ), 1671 Friedel pairs
Flack parameter: −0.01 (7)

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808035800/ng2508sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808035800/ng2508Isup2.hkl

checkCIF report

Comment top

6β-Acetoxy-3α-paramethylbenzene sulfonyloxytropane, a racemic analog of Baogongteng A, prepared in our laboratory (Yang et al., 1998), is a potent muscarinic receptor agonist and has been shown to be a promising candidate as a new antiglaucoma agent in our previous preclinical studies. Recently, we resolved the racemates and investigated the pharmacological characteristics of both enantiomers. The enantiomer (1R,3S,5R,6S) elicited agonistic activity on muscarinic receptors (Zhu et al., 2008). We report here the crystal structure of the bioactive enantiomer. The three-dimensional structure of the title compound is shown in Fig.1. The absolute stereochemistry has been confirmed by the structure determination, with absolute structure parameter -0.01 (7) (Flack, 1983). The tropane ring system adopts a conformation typical of 3α-substituted derivatives, with the piperidine ring in a chair-like shape and the pyrrolidine ring in an envelope form with nitrogen atom as the flap. Atoms N and C3 are displaced by 0.8762(0.0024) and 0.4602(0.0031) Å on opposite sides of the plane containing four atoms C1,C2, C4 and C5 (plane I), and N is deviated by 0.6435 (0.0029)Å from the mean plane through the other four atoms C1,C5,C6,C7 (plane II). The phenyl group C12 to C17 is planar to within 0.0078 (plane III). The dihedral angles between planes I—II and planes I-III are 67.58 (0.09)° and 28.67 (0.08)° respectively.

Related literature top

For the synthesis, see: Yang & Wang (1998); Xie et al. (2005). For the pharmacological activity, see: Zhu et al. (2008).

Experimental top

Preparation of the title compound has been described previously (Yang et al.,1998). 6β-Acetoxy-3 α-tropanol (11 g, 0.06 mol) was dissolved in 20 ml CHCl3, and 4-toluene sulfonyl chloride (13 g, 0.07 mol) in 8 ml pyridine were added. The mixture was stirred at room temperature for 72 h. The solvent was evaporated in vacou. The residue was dissolved in anhydrous ethanol and recrystallized to give the hydrochloride of racemates of the title compound. Then it was dissolved in 20% ammonium hydroxide, extracted with dichloromethane and the organic phase was dried over anhydrous sodium sulfate and evaporated in vacou to give racemates of the title compound. The racemates (9.8 g, 0.03 mol) and (-)-2,3-dibenzoyl-L-tartaric acid (11 g, 0.03 mol) were dissolved in methanol for 2 h. After disposing at room temperature for 3 h, the (-)-2,3-dibenzoyl-L-tartarate as precipitate was collected by filtration and recrystallized from anhydrous ethanol. The salt was converted into the title compound as colorless crystals, 30% yield, m.p. 403–405 K, [α]_D²⁰ -11.42 (c = 0.1313, CHCl₃), by treatment with 20% ammonium hydroxide as described above. The enantiomeric excess of the title compound was 98.05% (Xie et al., 2005). Crystals suitable for X-ray analysis were obtained by slow crystallization from acetone.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. Ellipsoid plot.

(1R,3S,5R,6S)-8-methyl-3-(4-methylphenylsulfonyloxy)-8- azabicyclo[3.2.1]octan-6-yl acetate top

Crystal data top

C₁₇H₂₃NO₅S	D_x = 1.358 Mg m⁻³
M_r = 353.42	Melting point: 405 K
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3847 reflections
a = 6.9241 (6) Å	θ = 2.5–26.2°
b = 15.5069 (14) Å	µ = 0.21 mm⁻¹
c = 16.1020 (15) Å	T = 293 K
V = 1728.9 (3) Å³	P{rism, colorless
Z = 4	0.48 × 0.41 × 0.31 mm
F(000) = 752

Data collection top

Bruker SMART area-detector diffractometer	3770 independent reflections
Radiation source: fine-focus sealed tube	3238 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.066
ϕ and ω scans	θ_max = 27.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −6→8
T_min = 0.751, T_max = 1.000	k = −19→18
10216 measured reflections	l = −20→14

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.040	w = 1/[σ²(F_o²) + (0.0451P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.093	(Δ/σ)_max = 0.001
S = 0.97	Δρ_max = 0.20 e Å⁻³
3770 reflections	Δρ_min = −0.23 e Å⁻³
221 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0065 (11)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1671 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.01 (7)

Crystal data top

C₁₇H₂₃NO₅S	V = 1728.9 (3) Å³
M_r = 353.42	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.9241 (6) Å	µ = 0.21 mm⁻¹
b = 15.5069 (14) Å	T = 293 K
c = 16.1020 (15) Å	0.48 × 0.41 × 0.31 mm

Data collection top

Bruker SMART area-detector diffractometer	3770 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	3238 reflections with I > 2σ(I)
T_min = 0.751, T_max = 1.000	R_int = 0.066
10216 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	H-atom parameters constrained
wR(F²) = 0.093	Δρ_max = 0.20 e Å⁻³
S = 0.97	Δρ_min = −0.23 e Å⁻³
3770 reflections	Absolute structure: Flack (1983), 1671 Friedel pairs
221 parameters	Absolute structure parameter: −0.01 (7)
0 restraints

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
S1	0.96500 (8)	0.56721 (3)	0.57026 (3)	0.04821 (16)
O1	0.83603 (18)	0.75864 (9)	0.86913 (8)	0.0433 (3)
O2	1.1550 (2)	0.76965 (12)	0.85445 (11)	0.0663 (5)
O3	0.8477 (2)	0.62594 (8)	0.63122 (8)	0.0476 (4)
O4	1.1038 (2)	0.61718 (11)	0.52631 (10)	0.0613 (4)
O5	1.0274 (3)	0.49732 (10)	0.62094 (11)	0.0692 (5)
N8	0.6078 (2)	0.83046 (10)	0.71495 (11)	0.0423 (4)
C1	0.5182 (3)	0.74438 (13)	0.70783 (12)	0.0444 (5)
H1	0.3790	0.7481	0.7183	0.053*
C2	0.5559 (3)	0.71277 (14)	0.61955 (13)	0.0482 (5)
H2A	0.5003	0.6558	0.6130	0.058*
H2B	0.4918	0.7511	0.5807	0.058*
C3	0.7683 (3)	0.70892 (12)	0.59874 (13)	0.0447 (5)
H3	0.7838	0.7103	0.5383	0.054*
C4	0.8843 (3)	0.78262 (13)	0.63697 (12)	0.0429 (5)
H4A	1.0190	0.7657	0.6405	0.051*
H4B	0.8762	0.8326	0.6010	0.051*
C5	0.8130 (3)	0.80705 (12)	0.72301 (12)	0.0380 (4)
H5	0.8878	0.8554	0.7453	0.046*
C6	0.8169 (3)	0.72949 (12)	0.78367 (12)	0.0387 (4)
H6	0.9185	0.6882	0.7689	0.046*
C7	0.6163 (3)	0.68959 (13)	0.77502 (14)	0.0446 (5)
H7A	0.5459	0.6928	0.8270	0.053*
H7B	0.6250	0.6297	0.7579	0.053*
C9	0.5348 (3)	0.87927 (14)	0.78624 (13)	0.0528 (5)
H9A	0.5454	0.8448	0.8355	0.079*
H9B	0.4019	0.8940	0.7771	0.079*
H9C	0.6094	0.9310	0.7929	0.079*
C10	1.0149 (3)	0.77628 (12)	0.89615 (13)	0.0434 (5)
C11	1.0125 (3)	0.80429 (14)	0.98486 (14)	0.0530 (6)
H11A	0.9534	0.7603	1.0182	0.079*
H11B	0.9402	0.8568	0.9899	0.079*
H11C	1.1425	0.8137	1.0035	0.079*
C12	0.7863 (3)	0.53147 (12)	0.50065 (13)	0.0436 (5)
C13	0.6276 (3)	0.48904 (15)	0.53244 (15)	0.0596 (6)
H13	0.6197	0.4778	0.5891	0.072*
C14	0.4820 (3)	0.46356 (14)	0.48051 (16)	0.0593 (6)
H14	0.3746	0.4357	0.5025	0.071*
C15	0.4917 (3)	0.47852 (12)	0.39596 (14)	0.0463 (5)
C16	0.6542 (3)	0.51942 (13)	0.36492 (14)	0.0490 (5)
H16	0.6642	0.5288	0.3080	0.059*
C17	0.8019 (3)	0.54657 (12)	0.41651 (12)	0.0446 (5)
H17	0.9096	0.5745	0.3949	0.054*
C18	0.3260 (4)	0.45457 (15)	0.33942 (17)	0.0645 (7)
H18A	0.2196	0.4930	0.3490	0.097*
H18B	0.2863	0.3964	0.3508	0.097*
H18C	0.3667	0.4590	0.2826	0.097*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0516 (3)	0.0486 (3)	0.0444 (3)	0.0070 (2)	−0.0010 (3)	−0.0041 (2)
O1	0.0368 (7)	0.0631 (8)	0.0300 (7)	−0.0006 (6)	−0.0012 (6)	0.0014 (6)
O2	0.0381 (8)	0.0992 (13)	0.0617 (10)	−0.0063 (9)	0.0096 (8)	−0.0149 (10)
O3	0.0639 (9)	0.0453 (7)	0.0337 (7)	0.0072 (7)	0.0015 (7)	0.0006 (6)
O4	0.0454 (9)	0.0769 (10)	0.0615 (10)	−0.0050 (8)	0.0070 (8)	−0.0094 (9)
O5	0.0832 (12)	0.0597 (9)	0.0645 (11)	0.0239 (9)	−0.0145 (10)	−0.0013 (8)
N8	0.0422 (9)	0.0490 (9)	0.0358 (9)	0.0084 (7)	0.0006 (8)	−0.0016 (8)
C1	0.0341 (10)	0.0591 (12)	0.0400 (11)	0.0006 (9)	−0.0015 (9)	−0.0016 (9)
C2	0.0490 (12)	0.0551 (12)	0.0406 (11)	0.0020 (10)	−0.0097 (10)	−0.0017 (10)
C3	0.0588 (13)	0.0453 (11)	0.0301 (9)	0.0059 (9)	0.0002 (9)	0.0026 (9)
C4	0.0467 (11)	0.0474 (11)	0.0346 (10)	0.0008 (9)	0.0078 (9)	0.0048 (9)
C5	0.0385 (11)	0.0415 (10)	0.0341 (10)	−0.0026 (8)	0.0017 (9)	−0.0003 (8)
C6	0.0398 (11)	0.0459 (10)	0.0304 (9)	0.0017 (9)	0.0017 (8)	0.0026 (9)
C7	0.0438 (11)	0.0538 (12)	0.0361 (10)	−0.0082 (9)	0.0008 (9)	0.0032 (9)
C9	0.0546 (13)	0.0579 (12)	0.0458 (12)	0.0143 (10)	0.0057 (11)	−0.0063 (10)
C10	0.0411 (12)	0.0453 (11)	0.0439 (11)	−0.0006 (9)	−0.0037 (9)	0.0036 (9)
C11	0.0530 (14)	0.0634 (13)	0.0426 (12)	−0.0007 (11)	−0.0101 (11)	0.0016 (10)
C12	0.0497 (12)	0.0388 (10)	0.0424 (11)	0.0039 (9)	0.0068 (10)	−0.0026 (9)
C13	0.0732 (16)	0.0603 (14)	0.0453 (13)	−0.0174 (12)	0.0081 (12)	0.0037 (11)
C14	0.0588 (15)	0.0557 (12)	0.0636 (15)	−0.0159 (11)	0.0146 (13)	0.0027 (11)
C15	0.0481 (13)	0.0327 (9)	0.0581 (12)	0.0053 (9)	0.0031 (10)	−0.0041 (9)
C16	0.0544 (13)	0.0507 (11)	0.0420 (11)	0.0044 (10)	0.0067 (10)	−0.0022 (10)
C17	0.0444 (11)	0.0463 (11)	0.0433 (12)	0.0013 (9)	0.0126 (9)	−0.0023 (9)
C18	0.0541 (14)	0.0594 (14)	0.0800 (18)	−0.0012 (11)	−0.0065 (13)	0.0006 (13)

Geometric parameters (Å, º) top

S1—O4	1.4231 (16)	C6—H6	0.9800
S1—O5	1.4239 (16)	C7—H7A	0.9700
S1—O3	1.5663 (14)	C7—H7B	0.9700
S1—C12	1.759 (2)	C9—H9A	0.9600
O1—C10	1.341 (2)	C9—H9B	0.9600
O1—C6	1.454 (2)	C9—H9C	0.9600
O2—C10	1.184 (2)	C10—C11	1.493 (3)
O3—C3	1.494 (2)	C11—H11A	0.9600
N8—C9	1.465 (2)	C11—H11B	0.9600
N8—C5	1.472 (2)	C11—H11C	0.9600
N8—C1	1.476 (3)	C12—C13	1.379 (3)
C1—C2	1.526 (3)	C12—C17	1.379 (3)
C1—C7	1.534 (3)	C13—C14	1.368 (3)
C1—H1	0.9800	C13—H13	0.9300
C2—C3	1.510 (3)	C14—C15	1.383 (3)
C2—H2A	0.9700	C14—H14	0.9300
C2—H2B	0.9700	C15—C16	1.385 (3)
C3—C4	1.527 (3)	C15—C18	1.511 (3)
C3—H3	0.9800	C16—C17	1.383 (3)
C4—C5	1.519 (3)	C16—H16	0.9300
C4—H4A	0.9700	C17—H17	0.9300
C4—H4B	0.9700	C18—H18A	0.9600
C5—C6	1.550 (3)	C18—H18B	0.9600
C5—H5	0.9800	C18—H18C	0.9600
C6—C7	1.526 (3)

O4—S1—O5	119.62 (11)	C5—C6—H6	111.5
O4—S1—O3	110.21 (9)	C6—C7—C1	104.05 (16)
O5—S1—O3	103.94 (9)	C6—C7—H7A	110.9
O4—S1—C12	109.26 (10)	C1—C7—H7A	110.9
O5—S1—C12	109.81 (10)	C6—C7—H7B	110.9
O3—S1—C12	102.57 (9)	C1—C7—H7B	110.9
C10—O1—C6	117.04 (15)	H7A—C7—H7B	109.0
C3—O3—S1	118.18 (12)	N8—C9—H9A	109.5
C9—N8—C5	113.03 (17)	N8—C9—H9B	109.5
C9—N8—C1	112.53 (16)	H9A—C9—H9B	109.5
C5—N8—C1	100.92 (14)	N8—C9—H9C	109.5
N8—C1—C2	106.91 (17)	H9A—C9—H9C	109.5
N8—C1—C7	105.06 (16)	H9B—C9—H9C	109.5
C2—C1—C7	113.78 (17)	O2—C10—O1	123.71 (19)
N8—C1—H1	110.3	O2—C10—C11	125.2 (2)
C2—C1—H1	110.3	O1—C10—C11	111.09 (18)
C7—C1—H1	110.3	C10—C11—H11A	109.5
C3—C2—C1	112.71 (17)	C10—C11—H11B	109.5
C3—C2—H2A	109.1	H11A—C11—H11B	109.5
C1—C2—H2A	109.1	C10—C11—H11C	109.5
C3—C2—H2B	109.1	H11A—C11—H11C	109.5
C1—C2—H2B	109.1	H11B—C11—H11C	109.5
H2A—C2—H2B	107.8	C13—C12—C17	120.5 (2)
O3—C3—C2	108.34 (16)	C13—C12—S1	118.30 (17)
O3—C3—C4	108.07 (16)	C17—C12—S1	121.17 (16)
C2—C3—C4	113.17 (17)	C14—C13—C12	119.9 (2)
O3—C3—H3	109.1	C14—C13—H13	120.1
C2—C3—H3	109.1	C12—C13—H13	120.1
C4—C3—H3	109.1	C13—C14—C15	121.2 (2)
C5—C4—C3	112.55 (16)	C13—C14—H14	119.4
C5—C4—H4A	109.1	C15—C14—H14	119.4
C3—C4—H4A	109.1	C14—C15—C16	118.1 (2)
C5—C4—H4B	109.1	C14—C15—C18	121.0 (2)
C3—C4—H4B	109.1	C16—C15—C18	120.8 (2)
H4A—C4—H4B	107.8	C17—C16—C15	121.6 (2)
N8—C5—C4	107.15 (17)	C17—C16—H16	119.2
N8—C5—C6	105.28 (15)	C15—C16—H16	119.2
C4—C5—C6	112.08 (16)	C12—C17—C16	118.72 (19)
N8—C5—H5	110.7	C12—C17—H17	120.6
C4—C5—H5	110.7	C16—C17—H17	120.6
C6—C5—H5	110.7	C15—C18—H18A	109.5
O1—C6—C7	107.18 (16)	C15—C18—H18B	109.5
O1—C6—C5	110.90 (16)	H18A—C18—H18B	109.5
C7—C6—C5	103.96 (15)	C15—C18—H18C	109.5
O1—C6—H6	111.5	H18A—C18—H18C	109.5
C7—C6—H6	111.5	H18B—C18—H18C	109.5

O4—S1—O3—C3	47.59 (16)	N8—C5—C6—C7	24.8 (2)
O5—S1—O3—C3	176.95 (14)	C4—C5—C6—C7	−91.32 (19)
C12—S1—O3—C3	−68.65 (15)	O1—C6—C7—C1	120.02 (17)
C9—N8—C1—C2	162.61 (17)	C5—C6—C7—C1	2.53 (19)
C5—N8—C1—C2	−76.63 (18)	N8—C1—C7—C6	−29.1 (2)
C9—N8—C1—C7	−76.2 (2)	C2—C1—C7—C6	87.5 (2)
C5—N8—C1—C7	44.6 (2)	C6—O1—C10—O2	0.3 (3)
N8—C1—C2—C3	57.9 (2)	C6—O1—C10—C11	−179.30 (16)
C7—C1—C2—C3	−57.6 (2)	O4—S1—C12—C13	−173.64 (16)
S1—O3—C3—C2	128.33 (15)	O5—S1—C12—C13	53.3 (2)
S1—O3—C3—C4	−108.70 (15)	O3—S1—C12—C13	−56.72 (18)
C1—C2—C3—O3	82.9 (2)	O4—S1—C12—C17	5.3 (2)
C1—C2—C3—C4	−36.9 (2)	O5—S1—C12—C17	−127.77 (18)
O3—C3—C4—C5	−83.20 (19)	O3—S1—C12—C17	122.19 (17)
C2—C3—C4—C5	36.8 (2)	C17—C12—C13—C14	−1.7 (3)
C9—N8—C5—C4	−162.88 (16)	S1—C12—C13—C14	177.25 (17)
C1—N8—C5—C4	76.72 (17)	C12—C13—C14—C15	0.9 (4)
C9—N8—C5—C6	77.6 (2)	C13—C14—C15—C16	0.6 (3)
C1—N8—C5—C6	−42.76 (19)	C13—C14—C15—C18	−176.7 (2)
C3—C4—C5—N8	−57.7 (2)	C14—C15—C16—C17	−1.4 (3)
C3—C4—C5—C6	57.3 (2)	C18—C15—C16—C17	175.95 (18)
C10—O1—C6—C7	164.05 (16)	C13—C12—C17—C16	0.9 (3)
C10—O1—C6—C5	−83.1 (2)	S1—C12—C17—C16	−177.98 (15)
N8—C5—C6—O1	−90.05 (18)	C15—C16—C17—C12	0.6 (3)
C4—C5—C6—O1	153.80 (16)

Experimental details

Crystal data
Chemical formula	C₁₇H₂₃NO₅S
M_r	353.42
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	6.9241 (6), 15.5069 (14), 16.1020 (15)
V (Å³)	1728.9 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.48 × 0.41 × 0.31

Data collection
Diffractometer	Bruker SMART area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2000)
T_min, T_max	0.751, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	10216, 3770, 3238
R_int	0.066
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.093, 0.97
No. of reflections	3770
No. of parameters	221
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.23
Absolute structure	Flack (1983), 1671 Friedel pairs
Absolute structure parameter	−0.01 (7)

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was supported by the Fund of the Science and Technology Commission of Shanghai Municipality (grant No. 06DZ19001) and the Shanghai Municipal Education Commission Foundation (grant No. 06BZ009). We thank the Shanghai Institute of Organic Chemistry for the X-ray data collection and analysis.

References

Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2000). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xie, Y., Yang, L. & Lu, Y. (2005). Acta Univ. Med. Sec. Shanghai, 25, 229–231. CAS Google Scholar
Yang, L. & Wang, H. (1998). Acta Pharm. Sin. 33, 832–835. CAS Google Scholar
Zhu, L., Yang, L., Cui, Y., Zheng, P., Niu, Y., Wang, H., Lu, Y., Ren, Q., Wei, P. & Chen, H. (2008). Acta Pharmacol. Sin. 29, 177–184. Web of Science CrossRef PubMed Google Scholar