1-Methyl-3-phenyl-sulfonyl-2-piperidone.

The piperidone ring in the title compound, C(12)H(15)NO(3)S, has a slightly distorted half-chair conformation with the methyl, carbonyl and phenyl-sulfonyl ring substituents occupying equatorial, equatorial and axial positions, respectively. Mol-ecules are connected into centrosymmetric dimers via C-H⋯O inter-actions and these associate into layers via C-H⋯O-S contacts. Further C-H⋯O inter-actions involving both the carbonyl and sulfonyl O atoms consolidate the crystal packing by providing connections between the layers.

Related literature

For related structures, see: Zukerman-Schpector et al. (1999 ▶, 2006 ▶). For related literature, see: Distefano et al. (1991 ▶); Olivato et al. (1992 ▶, 1997 ▶, 2003 ▶, 2004 ▶); Dal Colle et al. (1995 ▶). For ring conformational analysis, see: Cremer & Pople (1975 ▶). For the synthesis, see: Drabowicz et al. (1983 ▶); Zoretic & Soja (1976 ▶).

Experimental

Crystal data

C12H15NO3S

M = 253.32

Monoclinic,

a = 9.0191 (16) Å

b = 10.4920 (18) Å

c = 13.446 (3) Å

β = 107.861 (3)°

V = 1211.1 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 98 (2) K

0.25 × 0.18 × 0.10 mm

Data collection

Rigaku AFC12κ/SATURN724 diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.945, T max = 0.974

5193 measured reflections

2729 independent reflections

2549 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.118

S = 1.12

2729 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.45 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR92 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808009288/ng2443sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808009288/ng2443Isup2.hkl

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

C12H15NO3S	F000 = 536
Mr = 253.32	Dx = 1.389 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71070 Å
Hall symbol: -P 2yn	Cell parameters from 4417 reflections
a = 9.0191 (16) Å	θ = 2.4–40.6º
b = 10.4920 (18) Å	µ = 0.26 mm−1
c = 13.446 (3) Å	T = 98 (2) K
β = 107.861 (3)º	Block, colourless
V = 1211.1 (4) Å3	0.25 × 0.18 × 0.10 mm
Z = 4

Rigaku AFC12κ/SATURN724 diffractometer	2729 independent reflections
Radiation source: fine-focus sealed tube	2549 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.025
T = 98(2) K	θmax = 27.5º
ω scans	θmin = 2.5º
Absorption correction: multi-scan(ABSCOR; Higashi, 1995)	h = −10→11
Tmin = 0.945, Tmax = 0.974	k = −13→11
5193 measured reflections	l = −17→7

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047	H-atom parameters constrained
wR(F2) = 0.118	w = 1/[σ2(Fo2) + (0.0539P)2 + 0.7818P] where P = (Fo2 + 2Fc2)/3
S = 1.12	(Δ/σ)max < 0.001
2729 reflections	Δρmax = 0.39 e Å−3
154 parameters	Δρmin = −0.45 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.76305 (5)	0.20597 (4)	0.49677 (3)	0.01768 (15)
O1	1.13033 (15)	0.14856 (13)	0.56636 (9)	0.0186 (3)
O2	0.79732 (18)	0.33520 (13)	0.53443 (11)	0.0265 (3)
O3	0.60745 (15)	0.17739 (15)	0.43018 (11)	0.0275 (3)
N1	1.11807 (17)	0.30781 (15)	0.45077 (11)	0.0170 (3)
C1	1.0585 (2)	0.20646 (17)	0.48622 (13)	0.0147 (3)
C2	0.8952 (2)	0.16205 (17)	0.42479 (13)	0.0153 (3)
H2	0.8969	0.0669	0.4210	0.018*
C3	0.8348 (2)	0.21313 (18)	0.31267 (14)	0.0196 (4)
H3A	0.8843	0.1657	0.2676	0.024*
H3B	0.7208	0.1998	0.2850	0.024*
C4	0.8711 (2)	0.35463 (19)	0.30992 (14)	0.0214 (4)
H4A	0.8313	0.3865	0.2372	0.026*
H4B	0.8188	0.4027	0.3530	0.026*
C5	1.0457 (2)	0.37553 (19)	0.35160 (14)	0.0208 (4)
H5A	1.0942	0.3460	0.2989	0.025*
H5B	1.0668	0.4679	0.3625	0.025*
C6	1.2777 (2)	0.3460 (2)	0.50751 (14)	0.0213 (4)
H6A	1.3156	0.2956	0.5717	0.032*
H6B	1.2794	0.4367	0.5254	0.032*
H6C	1.3448	0.3314	0.4635	0.032*
C7	0.8027 (2)	0.10460 (17)	0.60682 (13)	0.0166 (3)
C8	0.9117 (2)	0.14160 (19)	0.70016 (14)	0.0199 (4)
H8	0.9681	0.2189	0.7041	0.024*
C9	0.9368 (2)	0.0641 (2)	0.78751 (14)	0.0211 (4)
H9	1.0114	0.0879	0.8516	0.025*
C10	0.8528 (2)	−0.04843 (19)	0.78116 (14)	0.0215 (4)
H10	0.8704	−0.1013	0.8411	0.026*
C11	0.7431 (2)	−0.08410 (19)	0.68753 (15)	0.0209 (4)
H11	0.6856	−0.1607	0.6839	0.025*
C12	0.7177 (2)	−0.00801 (18)	0.59943 (14)	0.0185 (4)
H12	0.6437	−0.0322	0.5352	0.022*

	U11	U22	U33	U12	U13	U23
S1	0.0168 (2)	0.0151 (3)	0.0225 (2)	0.00200 (16)	0.00796 (18)	0.00263 (16)
O1	0.0179 (6)	0.0205 (7)	0.0155 (6)	0.0007 (5)	0.0026 (5)	0.0026 (5)
O2	0.0382 (8)	0.0134 (7)	0.0353 (8)	0.0021 (6)	0.0223 (7)	0.0004 (6)
O3	0.0144 (6)	0.0339 (8)	0.0324 (7)	0.0022 (6)	0.0044 (6)	0.0120 (6)
N1	0.0153 (7)	0.0180 (8)	0.0159 (7)	−0.0018 (6)	0.0023 (6)	0.0013 (6)
C1	0.0153 (8)	0.0149 (9)	0.0147 (7)	−0.0002 (6)	0.0056 (6)	−0.0023 (6)
C2	0.0153 (8)	0.0141 (8)	0.0163 (8)	0.0000 (6)	0.0046 (6)	−0.0010 (6)
C3	0.0181 (9)	0.0224 (10)	0.0154 (8)	0.0001 (7)	0.0008 (7)	−0.0005 (7)
C4	0.0218 (9)	0.0215 (9)	0.0178 (8)	0.0016 (7)	0.0015 (7)	0.0027 (7)
C5	0.0242 (9)	0.0193 (9)	0.0174 (8)	−0.0015 (7)	0.0043 (7)	0.0044 (7)
C6	0.0187 (9)	0.0233 (10)	0.0205 (8)	−0.0054 (7)	0.0039 (7)	0.0003 (7)
C7	0.0180 (8)	0.0145 (8)	0.0194 (8)	0.0015 (7)	0.0090 (7)	0.0004 (7)
C8	0.0192 (9)	0.0192 (9)	0.0232 (9)	−0.0026 (7)	0.0096 (7)	−0.0035 (7)
C9	0.0197 (9)	0.0254 (10)	0.0191 (8)	−0.0010 (7)	0.0072 (7)	−0.0037 (7)
C10	0.0230 (9)	0.0243 (10)	0.0205 (8)	0.0027 (8)	0.0113 (7)	0.0037 (7)
C11	0.0204 (9)	0.0180 (9)	0.0274 (9)	−0.0019 (7)	0.0120 (7)	0.0002 (7)
C12	0.0173 (8)	0.0170 (9)	0.0214 (8)	−0.0014 (7)	0.0061 (7)	−0.0018 (7)

S1—O3	1.4457 (15)	C5—H5A	0.9900
S1—O2	1.4472 (15)	C5—H5B	0.9900
S1—C7	1.7674 (18)	C6—H6A	0.9800
S1—C2	1.8101 (18)	C6—H6B	0.9800
O1—C1	1.233 (2)	C6—H6C	0.9800
N1—C1	1.343 (2)	C7—C8	1.391 (3)
N1—C6	1.463 (2)	C7—C12	1.395 (3)
N1—C5	1.475 (2)	C8—C9	1.389 (3)
C1—C2	1.524 (2)	C8—H8	0.9500
C2—C3	1.534 (2)	C9—C10	1.391 (3)
C2—H2	1.0000	C9—H9	0.9500
C3—C4	1.523 (3)	C10—C11	1.393 (3)
C3—H3A	0.9900	C10—H10	0.9500
C3—H3B	0.9900	C11—C12	1.388 (3)
C4—C5	1.517 (3)	C11—H11	0.9500
C4—H4A	0.9900	C12—H12	0.9500
C4—H4B	0.9900
O3—S1—O2	118.26 (9)	N1—C5—C4	112.68 (15)
O3—S1—C7	107.61 (9)	N1—C5—H5A	109.1
O2—S1—C7	107.71 (9)	C4—C5—H5A	109.1
O3—S1—C2	106.81 (9)	N1—C5—H5B	109.1
O2—S1—C2	108.70 (8)	C4—C5—H5B	109.1
C7—S1—C2	107.28 (8)	H5A—C5—H5B	107.8
C1—N1—C6	117.93 (15)	N1—C6—H6A	109.5
C1—N1—C5	126.04 (15)	N1—C6—H6B	109.5
C6—N1—C5	115.53 (15)	H6A—C6—H6B	109.5
O1—C1—N1	122.70 (16)	N1—C6—H6C	109.5
O1—C1—C2	118.95 (16)	H6A—C6—H6C	109.5
N1—C1—C2	118.35 (15)	H6B—C6—H6C	109.5
C1—C2—C3	114.75 (15)	C8—C7—C12	121.42 (17)
C1—C2—S1	108.53 (11)	C8—C7—S1	119.54 (14)
C3—C2—S1	110.06 (12)	C12—C7—S1	118.96 (14)
C1—C2—H2	107.8	C9—C8—C7	119.10 (18)
C3—C2—H2	107.8	C9—C8—H8	120.4
S1—C2—H2	107.8	C7—C8—H8	120.4
C4—C3—C2	110.50 (15)	C8—C9—C10	120.03 (17)
C4—C3—H3A	109.6	C8—C9—H9	120.0
C2—C3—H3A	109.6	C10—C9—H9	120.0
C4—C3—H3B	109.6	C9—C10—C11	120.40 (17)
C2—C3—H3B	109.6	C9—C10—H10	119.8
H3A—C3—H3B	108.1	C11—C10—H10	119.8
C5—C4—C3	109.79 (16)	C12—C11—C10	120.17 (18)
C5—C4—H4A	109.7	C12—C11—H11	119.9
C3—C4—H4A	109.7	C10—C11—H11	119.9
C5—C4—H4B	109.7	C11—C12—C7	118.87 (17)
C3—C4—H4B	109.7	C11—C12—H12	120.6
H4A—C4—H4B	108.2	C7—C12—H12	120.6
C6—N1—C1—O1	3.1 (3)	C1—N1—C5—C4	21.7 (3)
C5—N1—C1—O1	174.61 (17)	C6—N1—C5—C4	−166.58 (16)
C6—N1—C1—C2	−177.19 (15)	C3—C4—C5—N1	−47.8 (2)
C5—N1—C1—C2	−5.7 (3)	O3—S1—C7—C8	−154.80 (15)
O1—C1—C2—C3	−163.27 (15)	O2—S1—C7—C8	−26.27 (17)
N1—C1—C2—C3	17.0 (2)	C2—S1—C7—C8	90.58 (15)
O1—C1—C2—S1	73.16 (18)	O3—S1—C7—C12	21.86 (17)
N1—C1—C2—S1	−106.55 (15)	O2—S1—C7—C12	150.39 (14)
O3—S1—C2—C1	172.73 (12)	C2—S1—C7—C12	−92.76 (15)
O2—S1—C2—C1	44.09 (14)	C12—C7—C8—C9	0.5 (3)
C7—S1—C2—C1	−72.12 (14)	S1—C7—C8—C9	177.05 (14)
O3—S1—C2—C3	46.40 (15)	C7—C8—C9—C10	−0.5 (3)
O2—S1—C2—C3	−82.24 (14)	C8—C9—C10—C11	0.0 (3)
C7—S1—C2—C3	161.55 (12)	C9—C10—C11—C12	0.5 (3)
C1—C2—C3—C4	−44.1 (2)	C10—C11—C12—C7	−0.5 (3)
S1—C2—C3—C4	78.63 (17)	C8—C7—C12—C11	0.0 (3)
C2—C3—C4—C5	59.6 (2)	S1—C7—C12—C11	−176.58 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1i	1.00	2.29	3.272 (2)	168
C6—H6B···O2ii	0.98	2.55	3.424 (3)	148
C11—H11···O3iii	0.95	2.62	3.224 (3)	122
C4—H4A···O1iv	0.99	2.48	3.328 (2)	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1i	1.00	2.29	3.272 (2)	168
C6—H6B⋯O2ii	0.98	2.55	3.424 (3)	148
C11—H11⋯O3iii	0.95	2.62	3.224 (3)	122
C4—H4A⋯O1iv	0.99	2.48	3.328 (2)	144

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .