4-Benzyl-8-phenyl-1-thia-4-aza-spiro-[4.5]decan-3-one.

In the title compound, C(21)H(23)NOS, the thia-zolidine ring adopts a twist conformation about one of its C-S bonds, while the cyclo-hexane ring has a chair conformation. The S and N atoms attached to the spiro C atom are in axial and equatorial orientations, respectively. The thia-zolidine ring forms dihedral angles of 86.24 (14) and 31.82 (15)° with the directly attached and remote terminal benzene rings, respectively. The dihedral angle between the two terminal benzene rings is 86.74 (14)°. In the crystal, the only significant directional inter-action is a weak C-H⋯π bond, which generates [010] chains.

Related literature

For the pharmacological activity of spiro­thia­zolidin-4-ones, see: Singh et al. (2006 ▶); Kasimogullari & Cesur (2004 ▶); Dandia et al. (2004 ▶); Sahu et al. (2006 ▶). For a related structure, see: Akkurt et al. (2008 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶). For the stability of the temperature controller used for data collection, see: Cosier & Glazer (1986 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C21H23NOS

M = 337.46

Monoclinic,

a = 9.8299 (9) Å

b = 15.3823 (14) Å

c = 12.0833 (10) Å

β = 108.717 (4)°

V = 1730.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.19 mm−1

T = 100 K

0.33 × 0.21 × 0.14 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.939, T max = 0.973

10508 measured reflections

3534 independent reflections

2144 reflections with I > 2σ(I)

R int = 0.080

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.145

S = 1.01

3534 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.71 e Å−3

Δρmin = −0.46 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812015358/hb6732sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812015358/hb6732Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812015358/hb6732Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C21H23NOS	F(000) = 720
Mr = 337.46	Dx = 1.295 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2184 reflections
a = 9.8299 (9) Å	θ = 2.6–29.6°
b = 15.3823 (14) Å	µ = 0.19 mm−1
c = 12.0833 (10) Å	T = 100 K
β = 108.717 (4)°	Block, colourless
V = 1730.4 (3) Å3	0.33 × 0.21 × 0.14 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	3534 independent reflections
Radiation source: fine-focus sealed tube	2144 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.080
φ and ω scans	θmax = 26.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→11
Tmin = 0.939, Tmax = 0.973	k = −16→19
10508 measured reflections	l = −15→15

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0622P)2 + 0.185P] where P = (Fo2 + 2Fc2)/3
3534 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 0.71 e Å−3
0 restraints	Δρmin = −0.46 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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.

	x	y	z	Uiso*/Ueq
S1	0.33380 (9)	−0.00046 (5)	0.85069 (6)	0.0253 (2)
O1	0.3626 (2)	0.18832 (13)	1.06649 (16)	0.0320 (6)
N1	0.3843 (3)	0.16539 (15)	0.88513 (19)	0.0211 (6)
C1	0.6646 (3)	0.29768 (18)	0.8312 (2)	0.0241 (7)
H1A	0.6047	0.3262	0.7633	0.029*
C2	0.8123 (4)	0.3003 (2)	0.8566 (3)	0.0296 (8)
H2A	0.8531	0.3314	0.8071	0.035*
C3	0.9005 (4)	0.2575 (2)	0.9542 (3)	0.0309 (8)
H3A	1.0017	0.2574	0.9702	0.037*
C4	0.8401 (4)	0.2147 (2)	1.0284 (3)	0.0310 (8)
H4A	0.9001	0.1868	1.0968	0.037*
C5	0.6923 (3)	0.21282 (19)	1.0028 (2)	0.0257 (7)
H5A	0.6517	0.1830	1.0536	0.031*
C6	0.6026 (3)	0.25385 (18)	0.9040 (2)	0.0211 (7)
C7	0.4415 (3)	0.25215 (19)	0.8761 (2)	0.0243 (7)
H7A	0.4148	0.2919	0.9303	0.029*
H7B	0.3962	0.2743	0.7958	0.029*
C8	0.3482 (3)	0.1418 (2)	0.9806 (2)	0.0251 (7)
C9	0.2885 (3)	0.0507 (2)	0.9689 (2)	0.0264 (7)
H9A	0.1830	0.0522	0.9514	0.032*
H9B	0.3313	0.0180	1.0425	0.032*
C10	0.3402 (3)	0.10667 (19)	0.7831 (2)	0.0210 (7)
C11	0.1909 (3)	0.13109 (19)	0.7013 (2)	0.0227 (7)
H11A	0.1912	0.1928	0.6780	0.027*
H11B	0.1202	0.1248	0.7436	0.027*
C12	0.1448 (3)	0.07408 (18)	0.5916 (2)	0.0212 (7)
H12A	0.0491	0.0928	0.5400	0.025*
H12B	0.1375	0.0128	0.6140	0.025*
C13	0.2545 (3)	0.08156 (19)	0.5260 (2)	0.0213 (7)
H13A	0.2647	0.1449	0.5116	0.026*
C14	0.4012 (3)	0.0504 (2)	0.6074 (2)	0.0242 (7)
H14A	0.3940	−0.0113	0.6284	0.029*
H14B	0.4731	0.0543	0.5661	0.029*
C15	0.4503 (3)	0.10522 (19)	0.7182 (2)	0.0221 (7)
H15A	0.4679	0.1655	0.6975	0.027*
H15B	0.5421	0.0817	0.7707	0.027*
C16	0.2087 (3)	0.0375 (2)	0.4081 (2)	0.0217 (7)
C17	0.2160 (3)	−0.05266 (19)	0.3972 (2)	0.0232 (7)
H17A	0.2473	−0.0877	0.4655	0.028*
C18	0.1782 (3)	−0.0918 (2)	0.2878 (2)	0.0260 (7)
H18A	0.1843	−0.1532	0.2818	0.031*
C19	0.1316 (3)	−0.0417 (2)	0.1874 (2)	0.0277 (7)
H19A	0.1060	−0.0684	0.1127	0.033*
C20	0.1226 (3)	0.0480 (2)	0.1970 (2)	0.0282 (8)
H20A	0.0910	0.0829	0.1286	0.034*
C21	0.1598 (3)	0.0866 (2)	0.3064 (2)	0.0248 (7)
H21A	0.1518	0.1478	0.3120	0.030*

	U11	U22	U33	U12	U13	U23
S1	0.0414 (5)	0.0194 (4)	0.0179 (4)	−0.0007 (4)	0.0134 (3)	0.0011 (4)
O1	0.0528 (15)	0.0301 (13)	0.0176 (11)	−0.0009 (11)	0.0177 (10)	−0.0058 (10)
N1	0.0318 (15)	0.0173 (13)	0.0172 (12)	−0.0043 (11)	0.0121 (10)	−0.0026 (11)
C1	0.041 (2)	0.0168 (16)	0.0145 (14)	−0.0017 (14)	0.0096 (14)	−0.0039 (13)
C2	0.049 (2)	0.0215 (18)	0.0238 (16)	−0.0070 (15)	0.0188 (15)	−0.0078 (14)
C3	0.0326 (19)	0.0268 (19)	0.0346 (18)	−0.0060 (14)	0.0125 (15)	−0.0142 (16)
C4	0.042 (2)	0.0256 (18)	0.0227 (16)	0.0024 (15)	0.0071 (15)	−0.0057 (14)
C5	0.041 (2)	0.0177 (17)	0.0195 (16)	−0.0028 (14)	0.0112 (14)	−0.0019 (14)
C6	0.0362 (19)	0.0131 (15)	0.0161 (14)	−0.0020 (13)	0.0111 (13)	−0.0019 (13)
C7	0.042 (2)	0.0149 (16)	0.0182 (15)	0.0026 (14)	0.0122 (13)	−0.0004 (13)
C8	0.0335 (19)	0.0257 (18)	0.0194 (15)	0.0028 (14)	0.0134 (13)	0.0015 (14)
C9	0.0354 (19)	0.0299 (19)	0.0162 (15)	−0.0036 (15)	0.0114 (13)	0.0005 (14)
C10	0.0338 (18)	0.0181 (16)	0.0142 (14)	−0.0021 (13)	0.0122 (13)	−0.0035 (13)
C11	0.0289 (18)	0.0246 (18)	0.0190 (15)	0.0016 (13)	0.0138 (13)	−0.0006 (13)
C12	0.0288 (18)	0.0197 (17)	0.0169 (14)	0.0002 (13)	0.0099 (12)	−0.0003 (13)
C13	0.0315 (18)	0.0196 (16)	0.0155 (14)	−0.0035 (13)	0.0112 (13)	−0.0025 (13)
C14	0.0309 (18)	0.0252 (17)	0.0208 (15)	−0.0009 (14)	0.0144 (13)	−0.0035 (14)
C15	0.0281 (18)	0.0228 (17)	0.0174 (14)	−0.0017 (13)	0.0101 (13)	−0.0017 (13)
C16	0.0262 (17)	0.0228 (16)	0.0192 (15)	−0.0034 (13)	0.0114 (12)	−0.0019 (14)
C17	0.0342 (18)	0.0212 (18)	0.0172 (15)	−0.0030 (14)	0.0125 (13)	0.0020 (14)
C18	0.0331 (19)	0.0217 (17)	0.0261 (16)	−0.0024 (14)	0.0139 (14)	−0.0054 (14)
C19	0.0327 (19)	0.035 (2)	0.0165 (15)	−0.0020 (15)	0.0094 (13)	−0.0069 (15)
C20	0.037 (2)	0.032 (2)	0.0176 (16)	0.0040 (15)	0.0103 (14)	0.0027 (15)
C21	0.0339 (19)	0.0221 (17)	0.0207 (16)	0.0000 (14)	0.0122 (13)	−0.0024 (14)

S1—C9	1.808 (3)	C11—C12	1.532 (4)
S1—C10	1.849 (3)	C11—H11A	0.9900
O1—C8	1.231 (3)	C11—H11B	0.9900
N1—C8	1.360 (3)	C12—C13	1.534 (4)
N1—C7	1.466 (4)	C12—H12A	0.9900
N1—C10	1.476 (3)	C12—H12B	0.9900
C1—C2	1.385 (4)	C13—C16	1.510 (4)
C1—C6	1.394 (4)	C13—C14	1.538 (4)
C1—H1A	0.9500	C13—H13A	1.0000
C2—C3	1.385 (4)	C14—C15	1.524 (4)
C2—H2A	0.9500	C14—H14A	0.9900
C3—C4	1.391 (4)	C14—H14B	0.9900
C3—H3A	0.9500	C15—H15A	0.9900
C4—C5	1.385 (4)	C15—H15B	0.9900
C4—H4A	0.9500	C16—C21	1.390 (4)
C5—C6	1.387 (4)	C16—C17	1.397 (4)
C5—H5A	0.9500	C17—C18	1.391 (4)
C6—C7	1.510 (4)	C17—H17A	0.9500
C7—H7A	0.9900	C18—C19	1.385 (4)
C7—H7B	0.9900	C18—H18A	0.9500
C8—C9	1.510 (4)	C19—C20	1.390 (4)
C9—H9A	0.9900	C19—H19A	0.9500
C9—H9B	0.9900	C20—C21	1.387 (4)
C10—C15	1.527 (4)	C20—H20A	0.9500
C10—C11	1.530 (4)	C21—H21A	0.9500
C9—S1—C10	90.75 (13)	C10—C11—H11B	109.2
C8—N1—C7	121.1 (2)	C12—C11—H11B	109.2
C8—N1—C10	117.3 (2)	H11A—C11—H11B	107.9
C7—N1—C10	120.8 (2)	C11—C12—C13	110.0 (2)
C2—C1—C6	120.9 (3)	C11—C12—H12A	109.7
C2—C1—H1A	119.5	C13—C12—H12A	109.7
C6—C1—H1A	119.5	C11—C12—H12B	109.7
C1—C2—C3	120.0 (3)	C13—C12—H12B	109.7
C1—C2—H2A	120.0	H12A—C12—H12B	108.2
C3—C2—H2A	120.0	C16—C13—C12	114.0 (2)
C2—C3—C4	119.6 (3)	C16—C13—C14	113.4 (2)
C2—C3—H3A	120.2	C12—C13—C14	108.4 (2)
C4—C3—H3A	120.2	C16—C13—H13A	106.8
C5—C4—C3	120.0 (3)	C12—C13—H13A	106.8
C5—C4—H4A	120.0	C14—C13—H13A	106.8
C3—C4—H4A	120.0	C15—C14—C13	110.9 (2)
C4—C5—C6	120.9 (3)	C15—C14—H14A	109.5
C4—C5—H5A	119.5	C13—C14—H14A	109.5
C6—C5—H5A	119.5	C15—C14—H14B	109.5
C5—C6—C1	118.5 (3)	C13—C14—H14B	109.5
C5—C6—C7	121.0 (3)	H14A—C14—H14B	108.0
C1—C6—C7	120.5 (3)	C14—C15—C10	112.5 (2)
N1—C7—C6	113.5 (2)	C14—C15—H15A	109.1
N1—C7—H7A	108.9	C10—C15—H15A	109.1
C6—C7—H7A	108.9	C14—C15—H15B	109.1
N1—C7—H7B	108.9	C10—C15—H15B	109.1
C6—C7—H7B	108.9	H15A—C15—H15B	107.8
H7A—C7—H7B	107.7	C21—C16—C17	118.0 (3)
O1—C8—N1	124.7 (3)	C21—C16—C13	120.3 (3)
O1—C8—C9	123.6 (3)	C17—C16—C13	121.7 (2)
N1—C8—C9	111.6 (2)	C18—C17—C16	120.9 (3)
C8—C9—S1	106.9 (2)	C18—C17—H17A	119.6
C8—C9—H9A	110.3	C16—C17—H17A	119.6
S1—C9—H9A	110.3	C19—C18—C17	120.3 (3)
C8—C9—H9B	110.3	C19—C18—H18A	119.9
S1—C9—H9B	110.3	C17—C18—H18A	119.9
H9A—C9—H9B	108.6	C18—C19—C20	119.4 (3)
N1—C10—C15	111.8 (2)	C18—C19—H19A	120.3
N1—C10—C11	110.7 (2)	C20—C19—H19A	120.3
C15—C10—C11	111.3 (2)	C21—C20—C19	120.0 (3)
N1—C10—S1	102.67 (17)	C21—C20—H20A	120.0
C15—C10—S1	110.1 (2)	C19—C20—H20A	120.0
C11—C10—S1	110.0 (2)	C20—C21—C16	121.4 (3)
C10—C11—C12	112.0 (2)	C20—C21—H21A	119.3
C10—C11—H11A	109.2	C16—C21—H21A	119.3
C12—C11—H11A	109.2
C6—C1—C2—C3	1.3 (4)	C9—S1—C10—C15	148.8 (2)
C1—C2—C3—C4	−2.3 (4)	C9—S1—C10—C11	−88.2 (2)
C2—C3—C4—C5	2.0 (4)	N1—C10—C11—C12	177.3 (2)
C3—C4—C5—C6	−0.6 (4)	C15—C10—C11—C12	52.4 (3)
C4—C5—C6—C1	−0.4 (4)	S1—C10—C11—C12	−69.9 (3)
C4—C5—C6—C7	−179.8 (3)	C10—C11—C12—C13	−57.8 (3)
C2—C1—C6—C5	0.1 (4)	C11—C12—C13—C16	−172.1 (2)
C2—C1—C6—C7	179.4 (3)	C11—C12—C13—C14	60.4 (3)
C8—N1—C7—C6	101.0 (3)	C16—C13—C14—C15	172.6 (2)
C10—N1—C7—C6	−89.9 (3)	C12—C13—C14—C15	−59.6 (3)
C5—C6—C7—N1	−47.5 (3)	C13—C14—C15—C10	55.7 (3)
C1—C6—C7—N1	133.2 (3)	N1—C10—C15—C14	−175.6 (2)
C7—N1—C8—O1	−1.7 (5)	C11—C10—C15—C14	−51.3 (3)
C10—N1—C8—O1	−171.2 (3)	S1—C10—C15—C14	71.0 (3)
C7—N1—C8—C9	178.6 (2)	C12—C13—C16—C21	104.1 (3)
C10—N1—C8—C9	9.1 (4)	C14—C13—C16—C21	−131.1 (3)
O1—C8—C9—S1	−164.6 (3)	C12—C13—C16—C17	−77.1 (4)
N1—C8—C9—S1	15.1 (3)	C14—C13—C16—C17	47.8 (4)
C10—S1—C9—C8	−26.3 (2)	C21—C16—C17—C18	1.2 (4)
C8—N1—C10—C15	−145.8 (3)	C13—C16—C17—C18	−177.7 (3)
C7—N1—C10—C15	44.7 (3)	C16—C17—C18—C19	−0.4 (4)
C8—N1—C10—C11	89.6 (3)	C17—C18—C19—C20	−0.2 (4)
C7—N1—C10—C11	−79.9 (3)	C18—C19—C20—C21	−0.2 (4)
C8—N1—C10—S1	−27.8 (3)	C19—C20—C21—C16	1.0 (5)
C7—N1—C10—S1	162.7 (2)	C17—C16—C21—C20	−1.5 (4)
C9—S1—C10—N1	29.6 (2)	C13—C16—C21—C20	177.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17A···Cg1i	0.95	2.72	3.565 (3)	149

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17A⋯Cg1i	0.95	2.72	3.565 (3)	149

Symmetry code: (i) .