[(3R,4S)-4-(4-Fluoro­phen­yl)-1-methyl­piperidin-3-yl]methyl 4-methyl­benzene­sulfonate

Qi, J.; Chen, H.; Zhang, C.

doi:10.1107/S1600536810038249

organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page o2660

doi:10.1107/S1600536810038249

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[(3R,4S)-4-(4-Fluorophenyl)-1-methylpiperidin-3-yl]methyl 4-methylbenzenesulfonate

Jianfeng Qi,^a Hanjing Chen ^a and Chen Zhang ^a ^*

^aDepartment of Medicinal Chemistry, College of Pharmaceutical Science, Zhejiang University, Hangzhou 310058, People's Republic of China
^*Correspondence e-mail: chenzhang@zju.edu.cn

(Received 19 May 2010; accepted 24 September 2010; online 30 September 2010)

In the title compound, C₂₀H₂₄FNO₃S, the piperidine ring adopts a chair conformation. The dihedral angle between the aromatic rings is 47.01 (17)°.

Related literature

For general background to the design and synthesis of vinyl sulfonate derivatives, see: Curzons (2003 ), Segura et al. (2003 ). For related structures, see: Wang & Kanagawa (1997 ).

Experimental

Crystal data

C₂₀H₂₄FNO₃S
M_r = 377.46
Monoclinic, P 2₁
a = 9.1590 (4) Å
b = 10.0764 (5) Å
c = 10.7644 (6) Å
β = 95.718 (1)°
V = 988.50 (9) Å³
Z = 2
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 296 K
0.32 × 0.26 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.931, T_max = 0.963
9742 measured reflections
4457 independent reflections
3114 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.084
S = 1.00
4457 reflections
238 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.14 e Å⁻³
Absolute structure: Flack (1983 ), 2086 Friedel pairs
Flack parameter: 0.05 (6)

Data collection: PROCESS-AUTO (Rigaku, 2006 ); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2007 ); 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, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810038249/kj2148sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810038249/kj2148Isup2.hkl

checkCIF report

Comment top

The title compound is a useful intermediate in preparing paroxetine [(3S,4R)-4-(4-fluorophenyl)-3-(3,4-methylenedioxyphenoxymethyl)- piperidine]. Paroxetine is a well-known selective serotonin reuptake inhibitor (SSRI) antidepressant, used world wide in therapeutics (Segura et al., 2003). In view of the above, ((3R,4S)-4-(4-fluorophenyl)-1-methylpiperidin-3-yl)methyl 4-methylbenzenesulfonate was synthesized and its crystal structure is reported here. A perspective view of the structure with the atomic numbering scheme is shown in Fig. 1. The dihedral angle between the two benzene rings is 47.01 (17)°. The piperidine ring adopts a chair conformation. The piperidine ring contains three planes (C2/C4/C5/C6, C3/C4/N1/C6, C2/C3/C5/N1), the first one of which is more planar than the other two.

Related literature top

For general background to the design and synthesis of vinyl sulfonate derivatives, see: Curzons et al. (2003), Segura et al. (2003). For related structures, see: Wang & Kanagawa (1997).

Experimental top

To a stirred solution of trans-(-)-paroxo (10 g) in dichloromethane (50 ml) triethylamine (7 ml) was added. The mixture was cooled to 268 K. Toluenesulfonyl chloride (12 g) was slowly added and stirred for l h at 268 K. Methanesulfonic acid (4 ml) was then added gradually and the mixture was concentrated at about 323 K at atmospheric pressure. The residue was taken up in toluene, water was added and this was stirred for 30 minutes. The top toluene layer was separated. The pH of the aqueous layer was then adjusted to 9.0 with a saturated NaHCO₃ solution. The product was filtered, washed with water and dried to yield the title compound (13 g) as a white to off-white solid (m.p. 380-381 K).

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 2006); cell refinement: PROCESS-AUTO (Rigaku, 2006); data reduction: CrystalStructure (Rigaku/MSC, 2007); 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, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. The molecular structure of the title compound showing atom labels and 40% probability displacement ellipsoids.

[(3R,4S)-4-(4-Fluorophenyl)-1-methylpiperidin-3-yl]methyl 4-methylbenzenesulfonate top

Crystal data top

C₂₀H₂₄FNO₃S	F(000) = 400
M_r = 377.46	D_x = 1.268 Mg m⁻³
Monoclinic, P2₁	Melting point: 380 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 9.1590 (4) Å	Cell parameters from 7787 reflections
b = 10.0764 (5) Å	θ = 3.0–27.4°
c = 10.7644 (6) Å	µ = 0.19 mm⁻¹
β = 95.718 (1)°	T = 296 K
V = 988.50 (9) Å³	Chunk, yellow
Z = 2	0.32 × 0.26 × 0.20 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	4457 independent reflections
Radiation source: rolling anode	3114 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
Detector resolution: 10.00 pixels mm^-1	θ_max = 27.4°, θ_min = 3.0°
ω scans	h = −11→11
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −13→13
T_min = 0.931, T_max = 0.963	l = −13→13
9742 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.031	w = 1/[σ²(F_o²) + (0.0395P)² + 0.063P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.084	(Δ/σ)_max < 0.001
S = 1.00	Δρ_max = 0.17 e Å⁻³
4457 reflections	Δρ_min = −0.14 e Å⁻³
238 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0052 (13)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 2086 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.05 (6)

Crystal data top

C₂₀H₂₄FNO₃S	V = 988.50 (9) Å³
M_r = 377.46	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 9.1590 (4) Å	µ = 0.19 mm⁻¹
b = 10.0764 (5) Å	T = 296 K
c = 10.7644 (6) Å	0.32 × 0.26 × 0.20 mm
β = 95.718 (1)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	4457 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3114 reflections with I > 2σ(I)
T_min = 0.931, T_max = 0.963	R_int = 0.021
9742 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	H-atom parameters constrained
wR(F²) = 0.084	Δρ_max = 0.17 e Å⁻³
S = 1.00	Δρ_min = −0.14 e Å⁻³
4457 reflections	Absolute structure: Flack (1983), 2086 Friedel pairs
238 parameters	Absolute structure parameter: 0.05 (6)
1 restraint

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.

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	0.34071 (5)	0.65560 (6)	0.19254 (4)	0.05870 (14)
O1	0.37947 (12)	0.66249 (15)	0.33871 (9)	0.0550 (3)
C14	0.51158 (17)	0.6533 (2)	0.13267 (13)	0.0496 (4)
O2	0.2721 (2)	0.52973 (18)	0.17277 (14)	0.0832 (5)
C2	0.4586 (2)	0.77398 (17)	0.53214 (15)	0.0481 (4)
H2	0.4844	0.8619	0.5665	0.058*
O3	0.26443 (18)	0.77282 (18)	0.15090 (14)	0.0788 (5)
N1	0.3547 (2)	0.71908 (16)	0.72847 (16)	0.0659 (5)
C3	0.5921 (2)	0.68346 (16)	0.56744 (16)	0.0533 (5)
H3	0.5703	0.5965	0.5292	0.064*
C7	0.7277 (2)	0.73680 (18)	0.51511 (18)	0.0568 (5)
C4	0.6116 (2)	0.6639 (3)	0.70958 (16)	0.0684 (5)
H4A	0.6855	0.5963	0.7303	0.082*
H4B	0.6463	0.7460	0.7492	0.082*
C1	0.4245 (2)	0.79152 (17)	0.39340 (16)	0.0507 (4)
H1A	0.3462	0.8558	0.3764	0.061*
H1B	0.5105	0.8238	0.3571	0.061*
C15	0.5673 (2)	0.7700 (2)	0.08678 (18)	0.0595 (5)
H15	0.5152	0.8491	0.0888	0.071*
C6	0.3242 (2)	0.7278 (2)	0.59338 (18)	0.0615 (5)
H6A	0.2441	0.7895	0.5729	0.074*
H6B	0.2937	0.6414	0.5604	0.074*
C5	0.4712 (3)	0.62325 (19)	0.75996 (19)	0.0737 (7)
H5A	0.4409	0.5373	0.7260	0.088*
H5B	0.4878	0.6148	0.8500	0.088*
C8	0.7843 (2)	0.6761 (3)	0.41456 (18)	0.0696 (6)
H8	0.7424	0.5975	0.3828	0.083*
C19	0.5895 (3)	0.5365 (2)	0.12864 (18)	0.0630 (5)
H19	0.5529	0.4583	0.1595	0.076*
C9	0.9024 (3)	0.7304 (3)	0.3602 (2)	0.0862 (7)
H9	0.9399	0.6887	0.2931	0.103*
C17	0.7790 (2)	0.6507 (4)	0.03166 (18)	0.0795 (6)
C18	0.7223 (3)	0.5368 (3)	0.0783 (2)	0.0792 (7)
H18	0.7748	0.4580	0.0759	0.095*
C20	0.9241 (3)	0.6477 (6)	−0.0255 (3)	0.1361 (12)
H20A	0.9107	0.6047	−0.1054	0.204*
H20B	0.9953	0.5998	0.0285	0.204*
H20C	0.9579	0.7369	−0.0357	0.204*
F1	1.07463 (15)	0.9031 (2)	0.35259 (18)	0.1293 (7)
C13	0.2204 (3)	0.6809 (4)	0.7843 (2)	0.1021 (10)
H13A	0.1910	0.5934	0.7567	0.153*
H13B	0.1435	0.7428	0.7590	0.153*
H13C	0.2392	0.6815	0.8737	0.153*
C12	0.7948 (2)	0.8534 (2)	0.5606 (2)	0.0732 (6)
H12	0.7603	0.8954	0.6288	0.088*
C10	0.9617 (2)	0.8460 (3)	0.4074 (3)	0.0858 (7)
C16	0.7006 (3)	0.7662 (3)	0.0384 (2)	0.0751 (7)
H16	0.7389	0.8444	0.0092	0.090*
C11	0.9115 (3)	0.9079 (3)	0.5067 (3)	0.0885 (7)
H11	0.9551	0.9859	0.5379	0.106*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0645 (3)	0.0783 (3)	0.0327 (2)	−0.0102 (3)	0.00190 (16)	0.0008 (3)
O1	0.0736 (7)	0.0586 (6)	0.0328 (5)	−0.0118 (8)	0.0056 (5)	0.0006 (7)
C14	0.0649 (9)	0.0540 (9)	0.0294 (7)	−0.0033 (11)	0.0024 (6)	0.0024 (9)
O2	0.0960 (12)	0.1015 (12)	0.0521 (9)	−0.0489 (10)	0.0078 (8)	−0.0117 (8)
C2	0.0602 (10)	0.0463 (9)	0.0372 (9)	−0.0004 (8)	0.0026 (7)	−0.0028 (7)
O3	0.0729 (10)	0.1132 (13)	0.0492 (9)	0.0227 (9)	0.0005 (7)	0.0127 (9)
N1	0.0924 (13)	0.0687 (10)	0.0391 (9)	−0.0094 (9)	0.0187 (8)	−0.0068 (7)
C3	0.0747 (11)	0.0445 (11)	0.0392 (9)	0.0079 (9)	−0.0017 (8)	−0.0071 (7)
C7	0.0597 (11)	0.0611 (11)	0.0475 (11)	0.0165 (9)	−0.0053 (9)	−0.0066 (9)
C4	0.0977 (13)	0.0628 (10)	0.0419 (9)	0.0124 (14)	−0.0073 (9)	0.0007 (11)
C1	0.0588 (10)	0.0501 (10)	0.0429 (10)	−0.0019 (8)	0.0036 (8)	0.0031 (7)
C15	0.0787 (14)	0.0583 (11)	0.0409 (10)	−0.0056 (10)	0.0027 (9)	0.0054 (9)
C6	0.0715 (13)	0.0689 (11)	0.0452 (11)	−0.0076 (10)	0.0106 (9)	−0.0042 (8)
C5	0.1250 (19)	0.0585 (15)	0.0376 (10)	−0.0056 (12)	0.0081 (11)	0.0020 (8)
C8	0.0716 (12)	0.0842 (15)	0.0506 (11)	0.0210 (13)	−0.0051 (9)	−0.0139 (12)
C19	0.0824 (15)	0.0587 (12)	0.0467 (12)	−0.0019 (11)	0.0004 (10)	−0.0012 (9)
C9	0.0689 (14)	0.130 (2)	0.0600 (15)	0.0322 (14)	0.0061 (11)	−0.0080 (13)
C17	0.0626 (11)	0.1280 (19)	0.0472 (11)	−0.0052 (18)	0.0019 (8)	−0.0036 (16)
C18	0.0810 (17)	0.0940 (17)	0.0603 (14)	0.0232 (14)	−0.0049 (12)	−0.0148 (13)
C20	0.0691 (14)	0.253 (4)	0.0883 (19)	−0.003 (3)	0.0194 (13)	−0.009 (3)
F1	0.0667 (8)	0.1822 (18)	0.1440 (16)	0.0034 (10)	0.0364 (9)	0.0170 (13)
C13	0.122 (2)	0.131 (3)	0.0591 (14)	−0.040 (2)	0.0382 (13)	−0.0086 (15)
C12	0.0656 (12)	0.0774 (14)	0.0771 (15)	0.0049 (11)	0.0098 (11)	−0.0234 (11)
C10	0.0482 (12)	0.118 (2)	0.0909 (19)	0.0140 (13)	0.0073 (12)	0.0047 (16)
C16	0.0785 (16)	0.0988 (18)	0.0482 (13)	−0.0271 (14)	0.0079 (11)	0.0101 (12)
C11	0.0601 (13)	0.0933 (17)	0.112 (2)	−0.0020 (12)	0.0077 (13)	−0.0169 (15)

Geometric parameters (Å, º) top

S1—O3	1.4219 (18)	C6—H6A	0.9700
S1—O2	1.4220 (17)	C6—H6B	0.9700
S1—O1	1.5796 (10)	C5—H5A	0.9700
S1—C14	1.7510 (16)	C5—H5B	0.9700
O1—C1	1.469 (2)	C8—C9	1.392 (3)
C14—C19	1.379 (3)	C8—H8	0.9300
C14—C15	1.392 (3)	C19—C18	1.380 (4)
C2—C1	1.505 (2)	C19—H19	0.9300
C2—C6	1.527 (3)	C9—C10	1.362 (4)
C2—C3	1.542 (2)	C9—H9	0.9300
C2—H2	0.9800	C17—C16	1.374 (4)
N1—C5	1.454 (3)	C17—C18	1.375 (4)
N1—C6	1.456 (2)	C17—C20	1.519 (3)
N1—C13	1.474 (3)	C18—H18	0.9300
C3—C7	1.513 (3)	C20—H20A	0.9600
C3—C4	1.535 (2)	C20—H20B	0.9600
C3—H3	0.9800	C20—H20C	0.9600
C7—C8	1.387 (3)	F1—C10	1.368 (3)
C7—C12	1.392 (3)	C13—H13A	0.9600
C4—C5	1.501 (3)	C13—H13B	0.9600
C4—H4A	0.9700	C13—H13C	0.9600
C4—H4B	0.9700	C12—C11	1.380 (3)
C1—H1A	0.9700	C12—H12	0.9300
C1—H1B	0.9700	C10—C11	1.356 (4)
C15—C16	1.375 (3)	C16—H16	0.9300
C15—H15	0.9300	C11—H11	0.9300

O3—S1—O2	119.85 (9)	C2—C6—H6B	109.3
O3—S1—O1	109.40 (9)	H6A—C6—H6B	108.0
O2—S1—O1	103.91 (9)	N1—C5—C4	111.70 (17)
O3—S1—C14	108.92 (10)	N1—C5—H5A	109.3
O2—S1—C14	109.32 (12)	C4—C5—H5A	109.3
O1—S1—C14	104.29 (6)	N1—C5—H5B	109.3
C1—O1—S1	117.67 (11)	C4—C5—H5B	109.3
C19—C14—C15	120.08 (17)	H5A—C5—H5B	107.9
C19—C14—S1	120.46 (16)	C7—C8—C9	121.4 (2)
C15—C14—S1	119.45 (17)	C7—C8—H8	119.3
C1—C2—C6	111.55 (15)	C9—C8—H8	119.3
C1—C2—C3	113.27 (14)	C14—C19—C18	119.3 (2)
C6—C2—C3	111.54 (15)	C14—C19—H19	120.4
C1—C2—H2	106.7	C18—C19—H19	120.4
C6—C2—H2	106.7	C10—C9—C8	118.5 (2)
C3—C2—H2	106.7	C10—C9—H9	120.8
C5—N1—C6	109.66 (15)	C8—C9—H9	120.8
C5—N1—C13	110.76 (19)	C16—C17—C18	117.99 (19)
C6—N1—C13	109.76 (18)	C16—C17—C20	121.4 (3)
C7—C3—C4	113.49 (15)	C18—C17—C20	120.6 (4)
C7—C3—C2	110.99 (14)	C17—C18—C19	121.7 (2)
C4—C3—C2	109.40 (15)	C17—C18—H18	119.2
C7—C3—H3	107.6	C19—C18—H18	119.2
C4—C3—H3	107.6	C17—C20—H20A	109.5
C2—C3—H3	107.6	C17—C20—H20B	109.5
C8—C7—C12	117.4 (2)	H20A—C20—H20B	109.5
C8—C7—C3	121.21 (18)	C17—C20—H20C	109.5
C12—C7—C3	121.27 (18)	H20A—C20—H20C	109.5
C5—C4—C3	112.10 (16)	H20B—C20—H20C	109.5
C5—C4—H4A	109.2	N1—C13—H13A	109.5
C3—C4—H4A	109.2	N1—C13—H13B	109.5
C5—C4—H4B	109.2	H13A—C13—H13B	109.5
C3—C4—H4B	109.2	N1—C13—H13C	109.5
H4A—C4—H4B	107.9	H13A—C13—H13C	109.5
O1—C1—C2	108.42 (13)	H13B—C13—H13C	109.5
O1—C1—H1A	110.0	C11—C12—C7	121.4 (2)
C2—C1—H1A	110.0	C11—C12—H12	119.3
O1—C1—H1B	110.0	C7—C12—H12	119.3
C2—C1—H1B	110.0	C11—C10—C9	122.2 (2)
H1A—C1—H1B	108.4	C11—C10—F1	118.5 (3)
C16—C15—C14	118.8 (2)	C9—C10—F1	119.3 (3)
C16—C15—H15	120.6	C17—C16—C15	122.2 (2)
C14—C15—H15	120.6	C17—C16—H16	118.9
N1—C6—C2	111.50 (16)	C15—C16—H16	118.9
N1—C6—H6A	109.3	C10—C11—C12	119.1 (2)
C2—C6—H6A	109.3	C10—C11—H11	120.4
N1—C6—H6B	109.3	C12—C11—H11	120.4

O3—S1—O1—C1	−38.54 (14)	C13—N1—C6—C2	177.1 (2)
O2—S1—O1—C1	−167.66 (14)	C1—C2—C6—N1	−176.31 (15)
C14—S1—O1—C1	77.84 (14)	C3—C2—C6—N1	55.9 (2)
O3—S1—C14—C19	−161.67 (15)	C6—N1—C5—C4	61.7 (2)
O2—S1—C14—C19	−29.00 (16)	C13—N1—C5—C4	−177.04 (18)
O1—S1—C14—C19	81.61 (16)	C3—C4—C5—N1	−57.2 (2)
O3—S1—C14—C15	17.09 (17)	C12—C7—C8—C9	−0.8 (3)
O2—S1—C14—C15	149.76 (15)	C3—C7—C8—C9	175.15 (18)
O1—S1—C14—C15	−99.62 (15)	C15—C14—C19—C18	−0.3 (3)
C1—C2—C3—C7	57.92 (18)	S1—C14—C19—C18	178.51 (16)
C6—C2—C3—C7	−175.24 (14)	C7—C8—C9—C10	−0.4 (3)
C1—C2—C3—C4	−176.09 (16)	C16—C17—C18—C19	1.1 (3)
C6—C2—C3—C4	−49.2 (2)	C20—C17—C18—C19	−178.8 (2)
C4—C3—C7—C8	129.5 (2)	C14—C19—C18—C17	−0.2 (3)
C2—C3—C7—C8	−106.83 (19)	C8—C7—C12—C11	1.1 (3)
C4—C3—C7—C12	−54.7 (2)	C3—C7—C12—C11	−174.8 (2)
C2—C3—C7—C12	68.9 (2)	C8—C9—C10—C11	1.3 (4)
C7—C3—C4—C5	174.59 (17)	C8—C9—C10—F1	−177.8 (2)
C2—C3—C4—C5	50.0 (2)	C18—C17—C16—C15	−1.7 (3)
S1—O1—C1—C2	−178.87 (11)	C20—C17—C16—C15	178.3 (2)
C6—C2—C1—O1	−61.63 (18)	C14—C15—C16—C17	1.3 (3)
C3—C2—C1—O1	65.21 (18)	C9—C10—C11—C12	−1.1 (4)
C19—C14—C15—C16	−0.3 (3)	F1—C10—C11—C12	178.1 (2)
S1—C14—C15—C16	−179.04 (15)	C7—C12—C11—C10	−0.2 (4)
C5—N1—C6—C2	−61.0 (2)

Experimental details

Crystal data
Chemical formula	C₂₀H₂₄FNO₃S
M_r	377.46
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	296
a, b, c (Å)	9.1590 (4), 10.0764 (5), 10.7644 (6)
β (°)	95.718 (1)
V (Å³)	988.50 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.32 × 0.26 × 0.20

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.931, 0.963
No. of measured, independent and observed [I > 2σ(I)] reflections	9742, 4457, 3114
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.084, 1.00
No. of reflections	4457
No. of parameters	238
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.14
Absolute structure	Flack (1983), 2086 Friedel pairs
Absolute structure parameter	0.05 (6)

Computer programs: PROCESS-AUTO (Rigaku, 2006), CrystalStructure (Rigaku/MSC, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Acknowledgements

Mr Jian-ming Gu of the X-ray crystallography facility of Zhejiang University is acknowledged for his assistance with the crystal structure analysis.

References

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