(1S,2R,4S)-1-[(Benzyl­amino)­meth­yl]-4-(prop-1-en-2-yl)cyclo­hexane-1,2-diol

Outouch, R.; Boualy, B.; Ali, M.A.; Firdoussi, L.E.; Rizzoli, C.

doi:10.1107/S1600536810052323

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 1| January 2011| Pages o195-o196

https://doi.org/10.1107/S1600536810052323

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(1S,2R,4S)-1-[(Benzylamino)methyl]-4-(prop-1-en-2-yl)cyclohexane-1,2-diol

Rachid Outouch,^a Brahim Boualy,^a Mustapha Ait Ali,^a Larbi El Firdoussi ^a and Corrado Rizzoli ^b ^*

^aEquipe de Chimie de Coordination et Catalyse, Département de Chimie, Faculté des Sciences Semlalia, BP 2390, 40001 Marrakech, Morocco, and ^bDipartimento di Chimica Generale ed Inorganica, Chimica Analitica, Chimica Fisica, Universitá degli Studi di Parma, Viale G. P. Usberti 17/A, I-43100 Parma, Italy
^*Correspondence e-mail: corrado.rizzoli@unipr.it

(Received 6 December 2010; accepted 13 December 2010; online 18 December 2010)

The title compound, C₁₇H₂₅NO₂, was synthesized by epoxidation of the double bond of (S)-perillyl alcohol [(S)-4-isopropenyl-1-cyclohexenylmethanol], followed by the oxirane ring-opening by benzylamine using [Ca(CF₃CO₂)₂] as catalyst under solvent-free condition at 313 K. The molecular conformation is stabilized by an intramolecular O—H⋯N hydrogen bond. In the crystal, molecules are linked by intermolecular 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 molecule 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_r = 275.38
Monoclinic, P 2₁
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[F² > 2σ(F²)] = 0.031
wR(F²) = 0.092
S = 1.08
1567 reflections
195 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.09 e Å⁻³

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) x, y, z+1; (ii) x+1, y, z.

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 ).

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810052323/gk2332Isup2.hkl

checkCIF report

Comment top

Aminodiols play important roles in drug therapy and drug research. For example, 5-(ω-hydroxyalkylamino) derivatives of mucochloric acids (2,3-dichloro-4-oxo-2-butenoic acid) have antibacterial and antiprotozoal activities (Gondela & Walczak, 2010). Other aminodiols have been found to act as HIV protease inhibitors (Kempf et al., 1992; Wang et al., 1995; Chen et al., 1996), or to exert renin inhibitor activity (Alexander & Liotta, 1996; Beaulieu et al., 1999). Furthermore, aminodiols may serve as useful starting materials for the synthesis of biologically active compounds, e. g. 3-amino-1,2-butanediol derivatives, which are key intermediates in the synthesis of the anticancer agent ES-285 (Allepuz et al., 2010). Chiral aminodiols and their derivatives also find excellent applications as catalysts for enantioselective transformations (Panev et al., 2001; Cherng et al., 1995, 1999; Pastó et al., 1996; Braga et al., 2003).

Among many different approaches developed for the synthesis of aminodiol derivatives (Canas et al., 1991; Panev et al., 2001; Kwon & Ko, 2003; Dias et al., 2008; Szakonyi et al., 2008), aminolysis of 1,2-epoxides represents one of the most valuable pathway to produce commercially important aminoalcohols and aminodiols from olefins (Ager et al., 1996; Bergmeier, 2000; Lee & Kang, 2004; Zhao et al., 2004; Fan & Hou, 2003; Kamal et al., 2005; Carree et al., 2004). As a contribution to this widespread area, we describe here the synthesis and crystal structure of the title new aminodiol derivative of perillyl alcohol. The synthetic methodology involves an epoxidation of the double bond, followed by the oxirane ring-opening by using benzylamine and Ca(CF₃CO₂)₂ as catalyst (Harrad et al., 2010) under solvent-free condition at 40°C.

The molecular structure of the title compound is shown in Fig. 1. The cyclohexane ring is in a chair conformation, with puckering parameters Q, θ and φ of 0.560 (2) Å, 2.6 (2)° and -167 (4)°, respectively (Cremer & Pople, 1975). The hydroxy groups at atoms C1 and C2 are both in axial positions. The molecular conformation is stabilized by an intramolecular O—H···N hydrogen bond (Table 1), generating a ring of S(6) graph set motif (Bernstein et al., 1995). In the crystal structure (Fig. 2), molecules are linked into chains parallel to the a axis by intermolecular N—H···O hydrogen bonds. The chains are further connected via O—H···O hydrogen bonding interactions to form sheets parallel to (010).

Related literature top

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 top

(S)-1,2-Epoxyperillyl alcohol was prepared from commercially available (S)-perillyl alcohol [(S)-4-isopropenyl-1-cyclohexenylmethanol, Fluka] using the procedure described in the literature (Bach et al., 1979). A mixture of benzylamine (5.1 mmol) and (S)-1,2-epoxyperillyl alcohol (5 mmol) was added to Ca(CF₃CO₂)₂ (0.25 mmol) under solvent-free conditions. The mixture was stirred at 40 °C for 72 h, then it was extracted with ethyl acetate (3 × 10 ml), dried over Na₂SO₄ and the solvent was removed under reduced pressure. Column chromatography (column 60 x 2.5 cm, hexane) of the residue on silica gel gave the title aminodiol in 52% yield (m. p. 429-430 K). Colourless crystals suitable for X-ray analysis were obtained on slow evaporation of the solvent.

Structure description top

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).

Computing details top

Data collection: AED (Belletti et al., 1993); cell refinement: AED (Belletti et al., 1993); data reduction: AED (Belletti et al., 1993); 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 (Sheldrick, 2008) and PARST95 (Nardelli, 1995).

Figures top

	Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 40% probability level.
	Fig. 2. Partial crystal packing of the title compound viewed approximately along the a axis. Intra- and intermolecular hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bondings are omitted for clarity.

(1S,2R,4S)-1-[(Benzylamino)methyl]-4-(prop-1-en-2- yl)cyclohexane-1,2-diol top

Crystal data top

C₁₇H₂₅NO₂	F(000) = 300
M_r = 275.38	D_x = 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

Data collection top

Siemens AED diffractometer	R_int = 0.010
Radiation source: fine-focus sealed tube	θ_max = 69.8°, θ_min = 3.6°
Graphite monochromator	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 top

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(F_o²) + (0.0584P)² + 0.0328P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.001
1567 reflections	Δρ_max = 0.16 e Å⁻³
195 parameters	Δρ_min = −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)

Crystal data top

C₁₇H₂₅NO₂	V = 808.50 (10) Å³
M_r = 275.38	Z = 2
Monoclinic, P2₁	Cu Kα radiation
a = 5.8281 (4) Å	µ = 0.58 mm⁻¹
b = 24.5421 (16) Å	T = 294 K
c = 5.8776 (4) Å	0.20 × 0.17 × 0.15 mm
β = 105.908 (4)°

Data collection top

Siemens AED diffractometer	R_int = 0.010
3041 measured reflections	3 standard reflections every 100 reflections
1567 independent reflections	intensity decay: 0.02%
1477 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.031	1 restraint
wR(F²) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.16 e Å⁻³
1567 reflections	Δρ_min = −0.09 e Å⁻³
195 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, y, z+1; (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₇H₂₅NO₂
M_r	275.38
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	294
a, b, c (Å)	5.8281 (4), 24.5421 (16), 5.8776 (4)
β (°)	105.908 (4)
V (Å³)	808.50 (10)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	0.58
Crystal size (mm)	0.20 × 0.17 × 0.15

Data collection
Diffractometer	Siemens AED
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3041, 1567, 1477
R_int	0.010
(sin θ/λ)_max (Å⁻¹)	0.609

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.092, 1.08
No. of reflections	1567
No. of parameters	195
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.09

Computer programs: AED (Belletti et al., 1993), SIR97 (Altomare et al., 1999), ORTEP-3 for Windows (Farrugia, 1997) and SCHAKAL97 (Keller, 1997), SHELXL97 (Sheldrick, 2008) and PARST95 (Nardelli, 1995).

Hydrogen-bond geometry (Å, º) top

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) x, y, z+1; (ii) x+1, y, z.

Acknowledgements

Financial support from the Universitá degli Studi di Parma is gratefully acknowledged.

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