3-Cyclo-propyl-1-(4-methyl-phenyl-sulfon-yl)piperidine-3,5-diol.

In the title compound, C(15)H(21)NO(4)S, both hy-droxy groups on the piperidine ring are located in axial positions, whereas the tosyl group and the cyclo-propane ring are in equatorial positions. An intra-molecular O-H⋯O hydrogen bond occurs. In the crystal, mol-ecules form inversion dimers via pairs of O-H⋯O hydrogen bonds, generating cyclic R(4) (4)(8) motifs, as noted previously in related diols.

Related literature

Aza­cyclo­hexa­nediol (piperidine­diol) derivatives are widely found in natural products and are often incorporated into drugs, see: Nagahama et al. (2003 ▶); Fukushima et al. (2001 ▶). For related structures, see: Hidekazu et al. (2005 ▶); Karin et al. (2006 ▶). Similar hydrogen bonding has been seen in related diols, see: Ferguson et al. (1993 ▶).

Experimental

Crystal data

C15H21NO4S

M = 311.39

Monoclinic,

a = 11.583 (5) Å

b = 5.598 (2) Å

c = 24.009 (9) Å

β = 102.905 (7)°

V = 1517.5 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 173 K

0.24 × 0.11 × 0.06 mm

Data collection

Rigaku MM007-HF CCD (Saturn 724+) diffractometer

Absorption correction: numerical (CrystalClear; Rigaku, 2002 ▶) T min = 0.947, T max = 0.986

9795 measured reflections

2676 independent reflections

2431 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.128

S = 1.23

2676 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.32 e Å−3

Data collection: CrystalClear (Rigaku, 2007 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811054420/gg2064sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811054420/gg2064Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811054420/gg2064Isup3.cml

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

C15H21NO4S	F(000) = 664
Mr = 311.39	Dx = 1.363 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2yn	Cell parameters from 345 reflections
a = 11.583 (5) Å	θ = 2.2–27.5°
b = 5.598 (2) Å	µ = 0.23 mm−1
c = 24.009 (9) Å	T = 173 K
β = 102.905 (7)°	Plate, colorless
V = 1517.5 (10) Å3	0.24 × 0.11 × 0.06 mm
Z = 4

Rigaku MM007-HF CCD (Saturn 724+) diffractometer	2676 independent reflections
Radiation source: rotating anode	2431 reflections with I > 2σ(I)
Confocal	Rint = 0.053
ω scans at fixed χ = 45°	θmax = 25.0°, θmin = 1.7°
Absorption correction: numerical (CrystalClear; Rigaku, 2002)	h = −13→13
Tmin = 0.947, Tmax = 0.986	k = −6→6
9795 measured reflections	l = −28→25

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H-atom parameters constrained
S = 1.23	w = 1/[σ2(Fo2) + (0.0211P)2 + 2.2306P] where P = (Fo2 + 2Fc2)/3
2676 reflections	(Δ/σ)max < 0.001
191 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

	x	y	z	Uiso*/Ueq
S1	0.48729 (7)	0.71212 (14)	0.21603 (3)	0.0254 (2)
O1	0.3693 (2)	0.8072 (4)	0.20391 (9)	0.0309 (6)
O2	0.5867 (2)	0.8711 (4)	0.22413 (9)	0.0333 (6)
O3	0.6103 (2)	0.5720 (4)	0.06890 (9)	0.0323 (6)
H3B	0.5388	0.5980	0.0535	0.049*
O4	0.3664 (2)	0.4775 (4)	0.04568 (9)	0.0293 (5)
H4	0.3722	0.4391	0.0126	0.044*
N1	0.4962 (2)	0.5392 (5)	0.16189 (10)	0.0239 (6)
C1	0.5488 (4)	0.0129 (7)	0.41161 (16)	0.0499 (11)
H1A	0.5012	0.0572	0.4390	0.075*
H1B	0.6325	0.0049	0.4312	0.075*
H1C	0.5231	−0.1434	0.3950	0.075*
C2	0.5327 (3)	0.1979 (6)	0.36466 (13)	0.0336 (8)
C3	0.6307 (3)	0.3092 (6)	0.35169 (13)	0.0314 (8)
H3A	0.7078	0.2742	0.3736	0.038*
C4	0.6166 (3)	0.4712 (6)	0.30688 (13)	0.0291 (8)
H4A	0.6839	0.5447	0.2976	0.035*
C5	0.5040 (3)	0.5246 (6)	0.27584 (12)	0.0242 (7)
C6	0.4056 (3)	0.4195 (6)	0.28916 (14)	0.0331 (8)
H6A	0.3282	0.4584	0.2682	0.040*
C7	0.4216 (3)	0.2568 (7)	0.33361 (14)	0.0390 (9)
H7A	0.3543	0.1840	0.3429	0.047*
C8	0.6136 (3)	0.4325 (6)	0.16365 (13)	0.0284 (8)
H8A	0.6255	0.2908	0.1890	0.034*
H8B	0.6768	0.5498	0.1788	0.034*
C9	0.6192 (3)	0.3603 (6)	0.10331 (13)	0.0296 (8)
H9A	0.6973	0.2823	0.1043	0.036*
C10	0.5208 (3)	0.1832 (6)	0.07993 (14)	0.0298 (8)
H10A	0.5367	0.0323	0.1018	0.036*
H10B	0.5213	0.1474	0.0396	0.036*
C11	0.3986 (3)	0.2754 (6)	0.08316 (13)	0.0262 (7)
C12	0.4001 (3)	0.3648 (6)	0.14376 (12)	0.0255 (7)
H12A	0.3231	0.4402	0.1445	0.031*
H12B	0.4118	0.2281	0.1706	0.031*
C13	0.3070 (3)	0.0790 (6)	0.06840 (13)	0.0308 (8)
H13A	0.3219	−0.0615	0.0948	0.037*
C14	0.2511 (3)	0.0174 (7)	0.00777 (14)	0.0370 (9)
H14A	0.2363	−0.1534	−0.0019	0.044*
H14B	0.2723	0.1158	−0.0227	0.044*
C15	0.1790 (3)	0.1328 (7)	0.04522 (15)	0.0415 (9)
H15A	0.1560	0.3021	0.0377	0.050*
H15B	0.1199	0.0330	0.0585	0.050*

	U11	U22	U33	U12	U13	U23
S1	0.0328 (5)	0.0215 (4)	0.0217 (4)	0.0001 (4)	0.0057 (3)	−0.0003 (3)
O1	0.0350 (14)	0.0271 (13)	0.0300 (12)	0.0092 (11)	0.0062 (10)	−0.0013 (10)
O2	0.0402 (15)	0.0251 (12)	0.0354 (13)	−0.0088 (11)	0.0105 (11)	−0.0012 (10)
O3	0.0342 (14)	0.0349 (14)	0.0274 (12)	0.0003 (11)	0.0057 (10)	0.0043 (10)
O4	0.0428 (14)	0.0237 (12)	0.0214 (11)	0.0061 (11)	0.0074 (10)	0.0032 (9)
N1	0.0276 (15)	0.0247 (15)	0.0201 (13)	0.0006 (12)	0.0066 (11)	0.0001 (11)
C1	0.058 (3)	0.050 (3)	0.040 (2)	0.000 (2)	0.0071 (19)	0.0173 (19)
C2	0.039 (2)	0.038 (2)	0.0236 (17)	0.0013 (18)	0.0070 (15)	0.0045 (16)
C3	0.0287 (19)	0.040 (2)	0.0234 (16)	0.0039 (16)	0.0011 (14)	0.0009 (15)
C4	0.0287 (19)	0.0338 (19)	0.0257 (17)	−0.0059 (16)	0.0083 (14)	−0.0033 (15)
C5	0.0292 (18)	0.0250 (17)	0.0182 (15)	−0.0005 (15)	0.0050 (13)	−0.0019 (13)
C6	0.0257 (19)	0.044 (2)	0.0289 (18)	−0.0042 (17)	0.0041 (14)	0.0028 (16)
C7	0.032 (2)	0.051 (2)	0.0355 (19)	−0.0083 (19)	0.0124 (16)	0.0103 (18)
C8	0.0316 (19)	0.0290 (19)	0.0243 (16)	0.0032 (15)	0.0058 (14)	0.0022 (15)
C9	0.034 (2)	0.0289 (19)	0.0269 (17)	0.0089 (15)	0.0084 (15)	0.0039 (14)
C10	0.040 (2)	0.0239 (18)	0.0265 (17)	0.0053 (15)	0.0102 (15)	−0.0025 (14)
C11	0.0379 (19)	0.0191 (17)	0.0216 (16)	0.0025 (15)	0.0064 (14)	0.0030 (13)
C12	0.0289 (19)	0.0237 (17)	0.0238 (16)	0.0004 (14)	0.0056 (14)	0.0006 (13)
C13	0.042 (2)	0.0240 (18)	0.0244 (17)	−0.0001 (16)	0.0030 (15)	0.0018 (14)
C14	0.045 (2)	0.032 (2)	0.0307 (19)	0.0002 (18)	0.0025 (16)	−0.0053 (16)
C15	0.038 (2)	0.041 (2)	0.046 (2)	−0.0009 (18)	0.0112 (18)	−0.0024 (18)

S1—O2	1.434 (2)	C6—H6A	0.9500
S1—O1	1.435 (2)	C7—H7A	0.9500
S1—N1	1.642 (3)	C8—C9	1.519 (4)
S1—C5	1.754 (3)	C8—H8A	0.9900
O3—C9	1.435 (4)	C8—H8B	0.9900
O3—H3B	0.8400	C9—C10	1.520 (5)
O4—C11	1.442 (4)	C9—H9A	1.0000
O4—H4	0.8401	C10—C11	1.526 (4)
N1—C12	1.471 (4)	C10—H10A	0.9900
N1—C8	1.478 (4)	C10—H10B	0.9900
C1—C2	1.511 (5)	C11—C13	1.514 (5)
C1—H1A	0.9800	C11—C12	1.535 (4)
C1—H1B	0.9800	C12—H12A	0.9900
C1—H1C	0.9800	C12—H12B	0.9900
C2—C7	1.375 (5)	C13—C15	1.493 (5)
C2—C3	1.389 (5)	C13—C14	1.495 (4)
C3—C4	1.389 (4)	C13—H13A	1.0000
C3—H3A	0.9500	C14—C15	1.502 (5)
C4—C5	1.383 (4)	C14—H14A	0.9900
C4—H4A	0.9500	C14—H14B	0.9900
C5—C6	1.382 (4)	C15—H15A	0.9900
C6—C7	1.384 (5)	C15—H15B	0.9900
O2—S1—O1	119.80 (14)	O3—C9—C10	112.0 (3)
O2—S1—N1	106.43 (13)	C8—C9—C10	109.8 (3)
O1—S1—N1	106.46 (13)	O3—C9—H9A	108.9
O2—S1—C5	108.78 (15)	C8—C9—H9A	108.9
O1—S1—C5	108.30 (14)	C10—C9—H9A	108.9
N1—S1—C5	106.28 (14)	C9—C10—C11	112.8 (3)
C9—O3—H3B	109.5	C9—C10—H10A	109.0
C11—O4—H4	109.0	C11—C10—H10A	109.0
C12—N1—C8	111.8 (2)	C9—C10—H10B	109.0
C12—N1—S1	116.65 (19)	C11—C10—H10B	109.0
C8—N1—S1	115.8 (2)	H10A—C10—H10B	107.8
C2—C1—H1A	109.5	O4—C11—C13	110.7 (3)
C2—C1—H1B	109.5	O4—C11—C10	110.3 (2)
H1A—C1—H1B	109.5	C13—C11—C10	110.6 (3)
C2—C1—H1C	109.5	O4—C11—C12	106.4 (2)
H1A—C1—H1C	109.5	C13—C11—C12	108.5 (3)
H1B—C1—H1C	109.5	C10—C11—C12	110.1 (3)
C7—C2—C3	118.9 (3)	N1—C12—C11	110.2 (2)
C7—C2—C1	120.9 (3)	N1—C12—H12A	109.6
C3—C2—C1	120.2 (3)	C11—C12—H12A	109.6
C4—C3—C2	120.4 (3)	N1—C12—H12B	109.6
C4—C3—H3A	119.8	C11—C12—H12B	109.6
C2—C3—H3A	119.8	H12A—C12—H12B	108.1
C5—C4—C3	119.5 (3)	C15—C13—C14	60.4 (2)
C5—C4—H4A	120.3	C15—C13—C11	121.7 (3)
C3—C4—H4A	120.3	C14—C13—C11	121.6 (3)
C6—C5—C4	120.7 (3)	C15—C13—H13A	114.2
C6—C5—S1	119.9 (2)	C14—C13—H13A	114.2
C4—C5—S1	119.3 (2)	C11—C13—H13A	114.2
C5—C6—C7	118.9 (3)	C13—C14—C15	59.8 (2)
C5—C6—H6A	120.6	C13—C14—H14A	117.8
C7—C6—H6A	120.6	C15—C14—H14A	117.8
C2—C7—C6	121.6 (3)	C13—C14—H14B	117.8
C2—C7—H7A	119.2	C15—C14—H14B	117.8
C6—C7—H7A	119.2	H14A—C14—H14B	114.9
N1—C8—C9	108.4 (3)	C13—C15—C14	59.9 (2)
N1—C8—H8A	110.0	C13—C15—H15A	117.8
C9—C8—H8A	110.0	C14—C15—H15A	117.8
N1—C8—H8B	110.0	C13—C15—H15B	117.8
C9—C8—H8B	110.0	C14—C15—H15B	117.8
H8A—C8—H8B	108.4	H15A—C15—H15B	114.9
O3—C9—C8	108.4 (3)
O2—S1—N1—C12	−177.7 (2)	C12—N1—C8—C9	64.1 (3)
O1—S1—N1—C12	−48.9 (2)	S1—N1—C8—C9	−159.1 (2)
C5—S1—N1—C12	66.4 (2)	N1—C8—C9—O3	63.8 (3)
O2—S1—N1—C8	47.6 (2)	N1—C8—C9—C10	−58.8 (3)
O1—S1—N1—C8	176.4 (2)	O3—C9—C10—C11	−66.3 (3)
C5—S1—N1—C8	−68.3 (2)	C8—C9—C10—C11	54.2 (4)
C7—C2—C3—C4	−2.1 (5)	C9—C10—C11—O4	66.2 (3)
C1—C2—C3—C4	177.1 (3)	C9—C10—C11—C13	−170.9 (3)
C2—C3—C4—C5	1.2 (5)	C9—C10—C11—C12	−50.9 (3)
C3—C4—C5—C6	0.3 (5)	C8—N1—C12—C11	−61.5 (3)
C3—C4—C5—S1	−175.3 (2)	S1—N1—C12—C11	162.1 (2)
O2—S1—C5—C6	156.2 (3)	O4—C11—C12—N1	−66.4 (3)
O1—S1—C5—C6	24.5 (3)	C13—C11—C12—N1	174.4 (3)
N1—S1—C5—C6	−89.5 (3)	C10—C11—C12—N1	53.2 (3)
O2—S1—C5—C4	−28.1 (3)	O4—C11—C13—C15	−32.1 (4)
O1—S1—C5—C4	−159.8 (2)	C10—C11—C13—C15	−154.7 (3)
N1—S1—C5—C4	86.1 (3)	C12—C11—C13—C15	84.4 (4)
C4—C5—C6—C7	−1.0 (5)	O4—C11—C13—C14	40.3 (4)
S1—C5—C6—C7	174.6 (3)	C10—C11—C13—C14	−82.3 (4)
C3—C2—C7—C6	1.5 (6)	C12—C11—C13—C14	156.8 (3)
C1—C2—C7—C6	−177.7 (3)	C11—C13—C14—C15	−111.1 (4)
C5—C6—C7—C2	0.1 (5)	C11—C13—C15—C14	110.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3B···O4	0.84	2.08	2.804 (3)	145.
O4—H4···O3i	0.84	2.01	2.837 (3)	167.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3B⋯O4	0.84	2.08	2.804 (3)	145
O4—H4⋯O3i	0.84	2.01	2.837 (3)	167

Symmetry code: (i) .