(1S,2R,4S)-1-[(Benzyl-amino)-meth-yl]-4-(prop-1-en-2-yl)cyclo-hexane-1,2-diol.

The title compound, C(17)H(25)NO(2), was synthesized by epoxidation of the double bond of (S)-perillyl alcohol [(S)-4-isopropenyl-1-cyclo-hexenyl-methanol], followed by the oxirane ring-opening by benzyl-amine using [Ca(CF(3)CO(2))(2)] as catalyst under solvent-free condition at 313 K. The mol-ecular conformation is stabilized by an intra-molecular O-H⋯N hydrogen bond. In the crystal, mol-ecules are linked by inter-molecular N-H⋯O hydrogen bonds, forming chains parallel to the a axis, which are further connected by O-H⋯O hydrogen bonds into sheets parallel to (010). The absolute configuration of the mol-ecule is known from the synthetic procedure.

Related literature

For the biological activity and applications of amino­diols, see: Alexander & Liotta (1996 ▶); Allepuz et al. (2010 ▶); Beaulieu et al. (1999 ▶); Braga et al. (2003 ▶); Chen et al. (1996 ▶); Cherng et al. (1995 ▶, 1999 ▶); Gondela & Walczak (2010 ▶); Kempf et al. (1992 ▶); Panev et al. (2001 ▶); Pastó et al. (1996 ▶); Wang et al. (1995 ▶). For the synthesis of amidiol derivatives, see: Ager et al. (1996 ▶); Bergmeier (2000 ▶); Canas et al. (1991 ▶); Carree et al. (2004 ▶); Dias et al. (2008 ▶); Fan & Hou (2003 ▶); Kamal et al. (2005 ▶); Kwon & Ko (2003 ▶); Lee & Kang (2004 ▶); Szakonyi et al. (2008 ▶); Zhao et al. (2004 ▶). For the use of [Ca(CF3CO2)2] as catalyst, see: Harrad et al. (2010 ▶). For the synthesis of (S)-1,2-ep­oxy­perillyl alcohol, see: Bach et al. (1979 ▶). For the graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995 ▶). For details of ring-puckering analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C17H25NO2

M = 275.38

Monoclinic,

a = 5.8281 (4) Å

b = 24.5421 (16) Å

c = 5.8776 (4) Å

β = 105.908 (4)°

V = 808.50 (10) Å3

Z = 2

Cu Kα radiation

μ = 0.58 mm−1

T = 294 K

0.20 × 0.17 × 0.15 mm

Data collection

Siemens AED diffractometer

3041 measured reflections

1567 independent reflections

1477 reflections with I > 2σ(I)

R int = 0.010

3 standard reflections every 100 reflections intensity decay: 0.02%

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.092

S = 1.08

1567 reflections

195 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.09 e Å−3

Data collection: AED (Belletti et al., 1993 ▶); cell refinement: AED; data reduction: AED; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and SCHAKAL97 (Keller, 1997 ▶); software used to prepare material for publication: SHELXL97 and PARST95 (Nardelli, 1995 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810052323/gk2332sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810052323/gk2332Isup2.hkl

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

C17H25NO2	F(000) = 300
Mr = 275.38	Dx = 1.131 Mg m−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2yb	Cell parameters from 48 reflections
a = 5.8281 (4) Å	θ = 12.6–38.8°
b = 24.5421 (16) Å	µ = 0.58 mm−1
c = 5.8776 (4) Å	T = 294 K
β = 105.908 (4)°	Block, colourless
V = 808.50 (10) Å3	0.20 × 0.17 × 0.15 mm
Z = 2

Siemens AED diffractometer	Rint = 0.010
Radiation source: fine-focus sealed tube	θmax = 69.8°, θmin = 3.6°
graphite	h = −7→7
θ/2θ scans	k = −28→29
3041 measured reflections	l = −7→1
1567 independent reflections	3 standard reflections every 100 reflections
1477 reflections with I > 2σ(I)	intensity decay: 0.02%

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)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.092	w = 1/[σ2(Fo2) + (0.0584P)2 + 0.0328P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
1567 reflections	Δρmax = 0.16 e Å−3
195 parameters	Δρmin = −0.09 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0091 (17)

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
O1	0.0402 (2)	0.20566 (7)	0.8285 (2)	0.0523 (3)
H1O	0.114 (5)	0.2089 (13)	0.971 (5)	0.075 (7)*
O2	0.2514 (2)	0.20737 (7)	0.3026 (2)	0.0573 (4)
H2O	0.379 (6)	0.1870 (13)	0.371 (6)	0.090 (9)*
N1	0.5565 (3)	0.15127 (7)	0.6459 (3)	0.0519 (4)
H1N	0.688 (4)	0.1715 (10)	0.719 (4)	0.055 (6)*
C1	0.2235 (3)	0.20879 (8)	0.7095 (2)	0.0432 (4)
C2	0.0876 (3)	0.21090 (9)	0.4445 (3)	0.0451 (4)
H2	−0.0219	0.1798	0.4075	0.054*
C3	−0.0551 (3)	0.26297 (9)	0.3798 (3)	0.0501 (4)
H3A	−0.1818	0.2634	0.4578	0.060*
H3B	−0.1284	0.2636	0.2104	0.060*
C4	0.0993 (4)	0.31396 (9)	0.4509 (4)	0.0551 (5)
H4	0.2232	0.3127	0.3669	0.066*
C5	0.2265 (4)	0.31182 (9)	0.7172 (4)	0.0580 (5)
H5A	0.3308	0.3432	0.7602	0.070*
H5B	0.1087	0.3137	0.8059	0.070*
C6	0.3724 (3)	0.25995 (9)	0.7830 (3)	0.0509 (4)
H6A	0.5009	0.2602	0.7073	0.061*
H6B	0.4433	0.2593	0.9527	0.061*
C7	−0.0400 (5)	0.36592 (11)	0.3773 (5)	0.0715 (6)
C8	−0.2383 (6)	0.37780 (15)	0.4831 (8)	0.1137 (13)
H8A	−0.3043	0.4130	0.4311	0.170*
H8B	−0.1791	0.3776	0.6524	0.170*
H8C	−0.3599	0.3505	0.4342	0.170*
C9	0.0179 (7)	0.40014 (13)	0.2250 (6)	0.0967 (10)
H9A	−0.0669	0.4324	0.1828	0.116*
H9B	0.1431	0.3917	0.1613	0.116*
C10	0.3697 (3)	0.15611 (9)	0.7684 (3)	0.0519 (5)
H10A	0.4431	0.1547	0.9377	0.062*
H10B	0.2628	0.1252	0.7264	0.062*
C11	0.6236 (4)	0.09492 (10)	0.6142 (4)	0.0654 (6)
H11A	0.7594	0.0955	0.5487	0.078*
H11B	0.4925	0.0778	0.4979	0.078*
C12	0.6868 (4)	0.05945 (9)	0.8337 (4)	0.0606 (5)
C13	0.9001 (5)	0.06545 (13)	1.0055 (6)	0.0835 (8)
H13	1.0082	0.0918	0.9871	0.100*
C14	0.9548 (6)	0.03319 (17)	1.2024 (6)	0.1002 (10)
H14	1.1006	0.0377	1.3152	0.120*
C15	0.8001 (7)	−0.00523 (12)	1.2363 (6)	0.0908 (9)
H15	0.8403	−0.0274	1.3698	0.109*
C16	0.5866 (7)	−0.01100 (13)	1.0734 (7)	0.1009 (10)
H16	0.4775	−0.0366	1.0966	0.121*
C17	0.5310 (6)	0.02089 (12)	0.8739 (6)	0.0914 (9)
H17	0.3842	0.0163	0.7629	0.110*

	U11	U22	U33	U12	U13	U23
O1	0.0435 (6)	0.0846 (9)	0.0303 (6)	−0.0047 (7)	0.0128 (5)	−0.0006 (6)
O2	0.0604 (7)	0.0859 (10)	0.0274 (5)	0.0089 (8)	0.0153 (5)	0.0031 (7)
N1	0.0461 (8)	0.0652 (10)	0.0451 (8)	0.0007 (7)	0.0137 (6)	0.0022 (7)
C1	0.0379 (7)	0.0653 (10)	0.0260 (7)	−0.0025 (8)	0.0085 (5)	0.0020 (8)
C2	0.0444 (8)	0.0633 (10)	0.0261 (7)	−0.0068 (8)	0.0070 (6)	−0.0051 (8)
C3	0.0436 (8)	0.0705 (11)	0.0320 (7)	−0.0022 (8)	0.0033 (6)	0.0000 (8)
C4	0.0514 (9)	0.0625 (11)	0.0504 (10)	−0.0026 (9)	0.0121 (8)	0.0001 (9)
C5	0.0557 (10)	0.0649 (12)	0.0496 (11)	−0.0066 (9)	0.0079 (8)	−0.0123 (9)
C6	0.0421 (8)	0.0730 (12)	0.0337 (8)	−0.0071 (9)	0.0037 (6)	−0.0057 (9)
C7	0.0732 (14)	0.0707 (14)	0.0665 (14)	0.0036 (11)	0.0122 (11)	0.0052 (11)
C8	0.089 (2)	0.092 (2)	0.169 (4)	0.0326 (18)	0.051 (2)	0.028 (2)
C9	0.134 (3)	0.0738 (17)	0.084 (2)	0.0154 (17)	0.0331 (19)	0.0160 (15)
C10	0.0495 (10)	0.0702 (12)	0.0365 (9)	0.0002 (8)	0.0126 (7)	0.0074 (8)
C11	0.0692 (13)	0.0728 (14)	0.0557 (11)	−0.0016 (10)	0.0196 (10)	−0.0077 (10)
C12	0.0617 (11)	0.0563 (11)	0.0642 (13)	0.0049 (9)	0.0179 (9)	−0.0071 (10)
C13	0.0620 (13)	0.103 (2)	0.0823 (17)	−0.0091 (13)	0.0138 (12)	0.0109 (15)
C14	0.0825 (18)	0.120 (3)	0.086 (2)	0.0014 (18)	0.0019 (15)	0.0123 (19)
C15	0.115 (2)	0.0723 (16)	0.0830 (19)	0.0220 (16)	0.0235 (17)	0.0135 (13)
C16	0.107 (2)	0.0737 (17)	0.116 (3)	−0.0139 (16)	0.021 (2)	0.0218 (17)
C17	0.0863 (17)	0.0703 (16)	0.102 (2)	−0.0157 (13)	−0.0009 (15)	0.0099 (15)

O1—C1	1.4301 (18)	C7—C9	1.336 (4)
O1—H1O	0.83 (3)	C7—C8	1.484 (5)
O2—C2	1.4319 (19)	C8—H8A	0.9600
O2—H2O	0.89 (3)	C8—H8B	0.9600
N1—C11	1.463 (3)	C8—H8C	0.9600
N1—C10	1.465 (2)	C9—H9A	0.9300
N1—H1N	0.92 (2)	C9—H9B	0.9300
C1—C6	1.520 (3)	C10—H10A	0.9700
C1—C10	1.535 (3)	C10—H10B	0.9700
C1—C2	1.5426 (19)	C11—C12	1.516 (3)
C2—C3	1.515 (3)	C11—H11A	0.9700
C2—H2	0.9800	C11—H11B	0.9700
C3—C4	1.531 (3)	C12—C17	1.376 (4)
C3—H3A	0.9700	C12—C13	1.378 (4)
C3—H3B	0.9700	C13—C14	1.366 (5)
C4—C7	1.510 (3)	C13—H13	0.9300
C4—C5	1.538 (3)	C14—C15	1.356 (5)
C4—H4	0.9800	C14—H14	0.9300
C5—C6	1.521 (3)	C15—C16	1.354 (5)
C5—H5A	0.9700	C15—H15	0.9300
C5—H5B	0.9700	C16—C17	1.373 (5)
C6—H6A	0.9700	C16—H16	0.9300
C6—H6B	0.9700	C17—H17	0.9300
C1—O1—H1O	103.5 (18)	C9—C7—C4	120.5 (3)
C2—O2—H2O	112 (2)	C8—C7—C4	117.7 (2)
C11—N1—C10	113.58 (17)	C7—C8—H8A	109.5
C11—N1—H1N	110.8 (14)	C7—C8—H8B	109.5
C10—N1—H1N	111.3 (15)	H8A—C8—H8B	109.5
O1—C1—C6	110.51 (15)	C7—C8—H8C	109.5
O1—C1—C10	106.71 (15)	H8A—C8—H8C	109.5
C6—C1—C10	113.15 (13)	H8B—C8—H8C	109.5
O1—C1—C2	104.49 (11)	C7—C9—H9A	120.0
C6—C1—C2	110.73 (15)	C7—C9—H9B	120.0
C10—C1—C2	110.82 (15)	H9A—C9—H9B	120.0
O2—C2—C3	108.21 (15)	N1—C10—C1	113.52 (15)
O2—C2—C1	110.28 (12)	N1—C10—H10A	108.9
C3—C2—C1	112.11 (15)	C1—C10—H10A	108.9
O2—C2—H2	108.7	N1—C10—H10B	108.9
C3—C2—H2	108.7	C1—C10—H10B	108.9
C1—C2—H2	108.7	H10A—C10—H10B	107.7
C2—C3—C4	112.31 (14)	N1—C11—C12	116.44 (18)
C2—C3—H3A	109.1	N1—C11—H11A	108.2
C4—C3—H3A	109.1	C12—C11—H11A	108.2
C2—C3—H3B	109.1	N1—C11—H11B	108.2
C4—C3—H3B	109.1	C12—C11—H11B	108.2
H3A—C3—H3B	107.9	H11A—C11—H11B	107.3
C7—C4—C3	112.49 (17)	C17—C12—C13	116.9 (2)
C7—C4—C5	113.05 (18)	C17—C12—C11	121.6 (2)
C3—C4—C5	109.44 (16)	C13—C12—C11	121.5 (2)
C7—C4—H4	107.2	C14—C13—C12	120.9 (3)
C3—C4—H4	107.2	C14—C13—H13	119.6
C5—C4—H4	107.2	C12—C13—H13	119.6
C6—C5—C4	111.52 (17)	C15—C14—C13	121.1 (3)
C6—C5—H5A	109.3	C15—C14—H14	119.4
C4—C5—H5A	109.3	C13—C14—H14	119.4
C6—C5—H5B	109.3	C16—C15—C14	119.2 (3)
C4—C5—H5B	109.3	C16—C15—H15	120.4
H5A—C5—H5B	108.0	C14—C15—H15	120.4
C1—C6—C5	112.55 (15)	C15—C16—C17	120.0 (3)
C1—C6—H6A	109.1	C15—C16—H16	120.0
C5—C6—H6A	109.1	C17—C16—H16	120.0
C1—C6—H6B	109.1	C16—C17—C12	121.8 (3)
C5—C6—H6B	109.1	C16—C17—H17	119.1
H6A—C6—H6B	107.8	C12—C17—H17	119.1
C9—C7—C8	121.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···N1	0.90 (3)	1.88 (3)	2.676 (2)	147 (3)
O1—H1O···O2i	0.83 (3)	1.89 (3)	2.721 (2)	171 (3)
N1—H1N···O1ii	0.92 (2)	2.15 (2)	3.037 (2)	164 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2O⋯N1	0.90 (3)	1.88 (3)	2.676 (2)	147 (3)
O1—H1O⋯O2i	0.83 (3)	1.89 (3)	2.721 (2)	171 (3)
N1—H1N⋯O1ii	0.92 (2)	2.15 (2)	3.037 (2)	164 (2)

Symmetry codes: (i) ; (ii) .