3-Cyclo­propyl-1-(4-methyl­phenyl­sulfon­yl)piperidine-3,5-diol

Wang, Y.; Lin, Y.-Y.

doi:10.1107/S1600536811054420

organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o231

doi:10.1107/S1600536811054420

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3-Cyclopropyl-1-(4-methylphenylsulfonyl)piperidine-3,5-diol

Yi Wang ^a ^* and Yong-Yue Lin ^a

^aCollege of Chemistry and Engineering, Yunnan Normal University, Kunming, People's Republic of China
^*Correspondence e-mail: sslwangyi@yahoo.cn

(Received 4 November 2011; accepted 18 December 2011; online 23 December 2011)

In the title compound, C₁₅H₂₁NO₄S, both hydroxy groups on the piperidine ring are located in axial positions, whereas the tosyl group and the cyclopropane ring are in equatorial positions. An intramolecular O—H⋯O hydrogen bond occurs. In the crystal, molecules form inversion dimers via pairs of O—H⋯O hydrogen bonds, generating cyclic R₄⁴(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_r = 311.39
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.069
wR(F²) = 0.128
S = 1.23
2676 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.32 e Å⁻³

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) -x+1, -y+1, -z.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811054420/gg2064sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811054420/gg2064Isup3.cml

checkCIF report

Comment top

Azacyclohexanediol (piperidinediol) derivatives are widely found in natural products and often incorporated into drugs (Nagahama et al., 2003). We report here the crystal structure of the title compound, a 1,3-piperidinediol derivative.

Bond lengths and angles were normal. The distance of N1—C8 and N1—C12 are 1.471 (4) and 1.478 (4) Å, respectively, which are in good agreement with normal N—C bond lengths [reported values range from 1.33 to 1.52 Å]. As shown as in Fig. 1, the two hydroxy groups in piperidine ring adopt a cis conformation. The twist angles of hydroxy groups and the piperidine are 112.0 (3) and 110.3 (3), respectively. Thus, the orientation of both hydroxy groups are axial in reference to the piperidine ring. A comparison with analogous 1,3-cyclohexanediol systems, shows that our observed system is in good agreement with similar 1,3-cyclohexanediols (Hidekazu et al., 2005; Karin et al., 2006). The cyclopropane C13—C15 planes is nearly coplanar with the azacyclohexane ring. A centrosymmetric dimer is generated by intermolecular O—H—O hydrogen bonding, and this has been seen previously in related diols (Ferguson et al., 1993), as shown in Fig. 2.

Related literature top

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 top

A mixture of N-(2-cyclopropylallyl)-4-methyl-N–(2-oxoethyl)benzenesulfonamide (1 mmol), ferric chloride hexahydrate (0.1mmol) was stirred in dichloromethane (5 ml) for 24 h. The mixture was concentrated and the residue was purified by flash column chromatography with silica gel to afford the title products (yield 55%). Single crystals suitable for X-ray diffraction were grown by slow diffusion of ether into a solution of the compound in dichloromethane.

Computing details top

Data collection: CrystalClear (Rigaku, 2007); cell refinement: CrystalClear (Rigaku, 2007); data reduction: CrystalClear (Rigaku, 2007); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The dimeric unit showing the hydrogen bonding as dashed lines.

3-Cyclopropyl-1-(4-methylphenylsulfonyl)piperidine-3,5-diol top

Crystal data top

C₁₅H₂₁NO₄S	F(000) = 664
M_r = 311.39	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0211P)² + 2.2306P] where P = (F_o² + 2F_c²)/3
2676 reflections	(Δ/σ)_max < 0.001
191 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₁₅H₂₁NO₄S	V = 1517.5 (10) Å³
M_r = 311.39	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.583 (5) Å	µ = 0.23 mm⁻¹
b = 5.598 (2) Å	T = 173 K
c = 24.009 (9) Å	0.24 × 0.11 × 0.06 mm
β = 102.905 (7)°

Data collection top

Rigaku MM007-HF CCD (Saturn 724+) diffractometer	2676 independent reflections
Absorption correction: numerical (CrystalClear; Rigaku, 2002)	2431 reflections with I > 2σ(I)
T_min = 0.947, T_max = 0.986	R_int = 0.053
9795 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.069	0 restraints
wR(F²) = 0.128	H-atom parameters constrained
S = 1.23	Δρ_max = 0.42 e Å⁻³
2676 reflections	Δρ_min = −0.32 e Å⁻³
191 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₅H₂₁NO₄S
M_r	311.39
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	11.583 (5), 5.598 (2), 24.009 (9)
β (°)	102.905 (7)
V (Å³)	1517.5 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.24 × 0.11 × 0.06

Data collection
Diffractometer	Rigaku MM007-HF CCD (Saturn 724+) diffractometer
Absorption correction	Numerical (CrystalClear; Rigaku, 2002)
T_min, T_max	0.947, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	9795, 2676, 2431
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.069, 0.128, 1.23
No. of reflections	2676
No. of parameters	191
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.32

Computer programs: CrystalClear (Rigaku, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3B···O4	0.84	2.08	2.804 (3)	144.7
O4—H4···O3ⁱ	0.84	2.01	2.837 (3)	166.9

Symmetry code: (i) −x+1, −y+1, −z.

Acknowledgements

The authors thank the China Postdoctoral Science Foundation (grant No. 20090460146) and Yunnan Normal University for financial support.

References

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