(7R,8S,8aS)-8-Hydr­oxy-7-phenyl­perhydro­indolizin-3-one

Švorc, Ľ.; Vrábel, V.; Marchalín, Š.; Šafář, P.; Kožíšek, J.

doi:10.1107/S1600536809018455

organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Pages o1368-o1369

doi:10.1107/S1600536809018455

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(7R,8S,8aS)-8-Hydroxy-7-phenylperhydroindolizin-3-one

Ľubomír Švorc,^a Viktor Vrábel,^a ^* Štefan Marchalín,^b Peter Šafář ^b and Jozef Kožíšek ^c

^aInstitute of Analytical Chemistry, Faculty of Chemical and Food Technology, Slovak Technical University, Radlinského 9, SK-81237 Bratislava, Slovak Republic, ^bInstitute of Organic Chemistry, Catalysis and Petrochemistry, Faculty of Chemical and Food Technology, Slovak Technical University, Radlinského 9, SK-81237 Bratislava, Slovak Republic, and ^cInstitute of Physical Chemistry and Chemical Physics, Faculty of Chemical and Food Technology, Slovak Technical University, Radlinského 9, SK-81237 Bratislava, Slovak Republic
^*Correspondence e-mail: viktor.vrabel@stuba.sk

(Received 12 May 2009; accepted 15 May 2009; online 23 May 2009)

In the title compound, C₁₄H₁₇NO₂, the six-membered ring of the indolizine system adopts a chair conformation. In the crystal, molecules form chains parallel to the b axis via intermolecular O—H⋯O hydrogen bonds. The absolute molecular configuration was assigned from the synthesis.

Related literature

For industrial uses of indolizines, see: Jaung & Jung (2003 ); Rotaru et al. (2005 ); Delattre et al. (2005 ); Kelin et al. (2001 ). For biological uses, see: Nash et al. (1988 ); Molyneux & James (1982 ); Harrell (1970 ); Ruprecht et al. (1989 ); Liu et al. (2007 ); Smith et al. (2007 ); Gupta et al. (2003 ); Rosseels et al. (1982 ); Oslund et al. (2008 ); Ostby et al. (2000 ). For synthesis of indolizines, see: Chuprakov & Gevorgyan (2007 ); Yan & Liu (2007 ). For the synthesis methods used, see: Šafář et al. (2009 ). For structures related to the title compound, see: Švorc et al. (2009 ). For comparison of molecular parameters, see: Camus et al. (2003 ); Lokaj et al. (1999 ); Brown & Corbridge (1954 ); Pedersen (1967 ). For a general analysis of puckering, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₄H₁₇NO₂
M_r = 231.29
Orthorhombic, P c a 2₁
a = 11.4164 (3) Å
b = 6.6372 (2) Å
c = 15.5118 (4) Å
V = 1175.38 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.60 × 0.56 × 0.13 mm

Data collection

Oxford Diffraction Gemini R CCD diffractometer
Absorption correction: analytical (Clark & Reid, 1995 ) T_min = 0.901, T_max = 0.989
26298 measured reflections
1632 independent reflections
1128 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.101
S = 1.03
1632 reflections
157 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.12 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1ⁱ	0.82	2.00	2.807 (2)	170
Symmetry code: (i) x, y+1, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2001 ); software used to prepare material for publication: enCIFer (Allen et al., 2004 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809018455/bg2260sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809018455/bg2260Isup2.hkl

checkCIF report

Comment top

Heterocycles are involved in a wide range of biologically important chemical reactions in living organisms, and therefore they form one of the most important and well investigated classes of organic compounds. One group of heterocycles, indolizines, has received much scientific attention during the recent years. They are known for their use as synthetic dyes (Jaung & Jung, 2003), fluorescent materials (Rotaru et al., 2005; Delattre et al., 2005) and also as key intermediates for the synthesis of indolizine based molecules (Kelin et al., 2001). Indolizines both synthetic and natural have also been ascribed with a number of useful biological activities such as antibacterial, antiviral, antiinflammatory (Nash et al., 1988; Molyneux & James, 1982), testosterone-3&-reductase inhibitors, 5-HT4 receptor antagonists, CNS depressants (Harrell et al., 1970), anti-HIV (Ruprecht et al., 1989), anti-cancer (Liu et al., 2007; Smith et al., 2007) and have been used for treating cardiovascular ailments (Gupta et al., 2003). For instance, aminoalkyloxybenzenesulfonylindolizine compounds such as fantofarone and butoprozine have been used for the treatment of hypertension, arrhythmia and angina pectoris (Rosseels et al., 1982). Several oxygenated indolizines have been shown to prevent, due to their strong anti-oxidative effects, the initiation of oxidation processes that lead to DNA damage (Oslund et al., 2008; Ostby et al., 2000). Consequently, synthesis of indolizines have attracted considerable attention and a number of synthetic methodologies have been developed for a variety of indolizines, making use of in particular, transition metal catalyzed reactions (Chuprakov & Gevorgyan, 2007; Yan & Liu, 2007). In addition, indolizines and their derivatives are important in the field of material science owing to their unique photophysical properties.

Based on these facts and in continutation of our interest in developing simple and efficient routes for the synthesis of novel indolizine derivatives, we report here the synthesis and molecular and crystal structure of the title compound, (I) (Fig. 1). A similar analysis of its enantiomer (the stereochemistry of atom C6 was confirmed as R) has already been published (Švorc et al., 2009). The absolute configuration of (I) was established by the synthesis and is depicted in the scheme and Fig. 1. The expected stereochemistry of atoms C5, C6 and C7 was confirmed as S, S and R, respectively (Fig. 1). The central six-membered N-heterocyclic ring is not planar and adopts a chair conformation (Cremer & Pople, 1975). A calculation of least-squares planes shows that this ring is puckered in such a manner that the four atoms C5, C6, C8 and C9 are coplanar to within 0.010 (2) Å, while atoms N1 and C7 are displaced from this plane on opposite sides, with out-of-plane displacements of -0.555 (2) and 0.711 (2) Å, respectively. The phenyl ring attached to the indolizine ring system is planar (mean deviation is 0.009 (2) Å). The N1—C5 and N1—C9 bonds are approximately equivalent (See supplementary material) and both are much longer than the N1—C2 bond. Moreover, the N1 atom is sp² hybridized, as evidenced by the sum of the valence angles around it [359.9 (2)°]. These data are consistent with conjugation of the lone-pair electrons on N1 with the adjacent carbonyl and agree with literature values for simple amides (Brown & Corbridge, 1954; Pedersen, 1967). The bond length of the carbonyl group C2═O1 is 1.236 (2) Å, respectively, is somewhat longer than typical carbonyl bonds. This may be due to the fact that atom O1 participates as acceptor in intermolecular hydrogen bonds with atom O2 as a donor. These intermolecular O—H···O hydrogen bonds link the molecules of (I) into extended chains, which run parallel to the b axis (Fig. 2) and help to stabilize the crystal structure of the compound. Bond lengths and angles in the indolizine ring system are in good agreement with values from the literature (Camus et al., 2003; Lokaj et al., 1999).

Related literature top

For industrial uses of indolizines, see: Jaung & Jung (2003); Rotaru et al. (2005); Delattre et al. (2005); Kelin et al. (2001). For biological uses, see: Nash et al. (1988); Molyneux & James (1982); Harrell et al. (1970); Ruprecht et al. (1989); Liu et al. (2007); Smith et al. (2007); Gupta et al. (2003); Rosseels et al. (1982); Oslund et al. (2008); Ostby et al. (2000). For synthesis of indolizines, see: Chuprakov & Gevorgyan (2007); Yan & Liu (2007). For the synthesis methods used, see: Šafář et al. (2009). For structures related to the title compound, see: Švorc et al. (2009). For comparison of molecular parameters, see: Camus et al. (2003); Lokaj et al. (1999); Brown & Corbridge (1954); Pedersen (1967). For a general analysis of puckering, see: Cremer & Pople (1975).

Experimental top

The title compound (7R,8S,8aS)-8-hydroxy-7-phenylhexahydroindolizin-3(5H)-one was prepared according literature procedures of Šafář et al. (2009).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2001); software used to prepare material for publication: enCIFer (Allen et al., 2004).

Figures top

	Fig. 1. Molecular structure of (I) with the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level (Brandenburg, 2001).
	Fig. 2. A packing of the molecule of (I), viewed along the b axis.

(7R,8S,8aS)-8-Hydroxy-7-phenylperhydroindolizin-3-one top

Crystal data top

C₁₄H₁₇NO₂	F(000) = 496
M_r = 231.29	D_x = 1.307 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 13180 reflections
a = 11.4164 (3) Å	θ = 3.3–29.4°
b = 6.6372 (2) Å	µ = 0.09 mm⁻¹
c = 15.5118 (4) Å	T = 298 K
V = 1175.38 (6) Å³	Block, white
Z = 4	0.60 × 0.56 × 0.13 mm

Data collection top

Oxford Diffraction Gemini R CCD diffractometer	1632 independent reflections
Radiation source: fine-focus sealed tube	1128 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Detector resolution: 10.4340 pixels mm^-1	θ_max = 29.4°, θ_min = 3.6°
Rotation method data acquisition using ω and ϕ scans	h = −15→15
Absorption correction: analytical (Clark & Reid, 1995)	k = −9→9
T_min = 0.901, T_max = 0.989	l = −20→21
26298 measured reflections

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)] = 0.035	H-atom parameters constrained
wR(F²) = 0.101	w = 1/[σ²(F_o²) + (0.0644P)² + 0.0334P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
1632 reflections	Δρ_max = 0.17 e Å⁻³
157 parameters	Δρ_min = −0.12 e Å⁻³
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.014 (4)

Crystal data top

C₁₄H₁₇NO₂	V = 1175.38 (6) Å³
M_r = 231.29	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 11.4164 (3) Å	µ = 0.09 mm⁻¹
b = 6.6372 (2) Å	T = 298 K
c = 15.5118 (4) Å	0.60 × 0.56 × 0.13 mm

Data collection top

Oxford Diffraction Gemini R CCD diffractometer	1632 independent reflections
Absorption correction: analytical (Clark & Reid, 1995)	1128 reflections with I > 2σ(I)
T_min = 0.901, T_max = 0.989	R_int = 0.023
26298 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	1 restraint
wR(F²) = 0.101	H-atom parameters constrained
S = 1.03	Δρ_max = 0.17 e Å⁻³
1632 reflections	Δρ_min = −0.12 e Å⁻³
157 parameters

Special details top

Experimental. face-indexed (CrysAlis RED; Oxford Diffraction, 2006)

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.

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

	x	y	z	U_iso*/U_eq
C2	0.2640 (2)	−0.3204 (3)	0.32882 (13)	0.0425 (5)
C3	0.21718 (19)	−0.1773 (3)	0.26133 (17)	0.0490 (5)
H3A	0.1398	−0.1296	0.2773	0.059*
H3B	0.2121	−0.2438	0.2058	0.059*
C4	0.3027 (2)	−0.0043 (4)	0.25750 (16)	0.0590 (6)
H4A	0.2626	0.1227	0.2670	0.071*
H4B	0.3409	0.0003	0.2017	0.071*
C5	0.3932 (2)	−0.0428 (3)	0.32948 (15)	0.0466 (5)
H5	0.4708	−0.0578	0.3033	0.056*
C6	0.40010 (17)	0.1156 (3)	0.40092 (13)	0.0400 (4)
H6	0.4340	0.2393	0.3771	0.048*
C7	0.47970 (18)	0.0382 (3)	0.47386 (13)	0.0421 (5)
H7	0.5558	0.0075	0.4478	0.051*
C8	0.4309 (2)	−0.1608 (3)	0.50890 (16)	0.0514 (6)
H8A	0.4814	−0.2100	0.5545	0.062*
H8B	0.3537	−0.1378	0.5332	0.062*
C9	0.4226 (2)	−0.3184 (3)	0.43821 (15)	0.0557 (6)
H9A	0.5006	−0.3569	0.4197	0.067*
H9B	0.3832	−0.4375	0.4600	0.067*
C10	0.50152 (16)	0.1935 (3)	0.54318 (14)	0.0407 (5)
C11	0.42606 (19)	0.2235 (4)	0.61193 (16)	0.0507 (5)
H11	0.3582	0.1464	0.6159	0.061*
C12	0.4494 (2)	0.3654 (4)	0.67466 (16)	0.0580 (6)
H12	0.3976	0.3833	0.7203	0.070*
C13	0.5498 (2)	0.4808 (4)	0.66972 (17)	0.0599 (7)
H13	0.5662	0.5754	0.7122	0.072*
C14	0.6248 (2)	0.4553 (4)	0.60216 (17)	0.0623 (7)
H14	0.6919	0.5343	0.5982	0.075*
C15	0.60156 (19)	0.3120 (4)	0.53928 (16)	0.0501 (5)
H15	0.6538	0.2951	0.4938	0.060*
N1	0.35736 (17)	−0.2359 (3)	0.36550 (12)	0.0473 (4)
O1	0.22237 (14)	−0.4869 (2)	0.34724 (11)	0.0545 (5)
O2	0.28771 (12)	0.1598 (2)	0.43433 (11)	0.0496 (4)
H2	0.2647	0.2673	0.4146	0.074*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C2	0.0503 (12)	0.0381 (10)	0.0391 (11)	0.0064 (9)	0.0004 (9)	−0.0066 (9)
C3	0.0507 (13)	0.0483 (11)	0.0480 (12)	0.0040 (9)	−0.0032 (10)	0.0014 (10)
C4	0.0858 (18)	0.0477 (12)	0.0436 (12)	−0.0088 (11)	−0.0148 (13)	0.0042 (10)
C5	0.0585 (13)	0.0404 (10)	0.0408 (10)	−0.0013 (9)	−0.0015 (10)	0.0023 (9)
C6	0.0488 (11)	0.0331 (10)	0.0382 (10)	−0.0015 (8)	0.0012 (9)	0.0038 (8)
C7	0.0395 (10)	0.0449 (12)	0.0419 (11)	0.0035 (8)	−0.0023 (9)	−0.0003 (9)
C8	0.0681 (15)	0.0384 (11)	0.0478 (11)	0.0032 (10)	−0.0163 (11)	0.0054 (9)
C9	0.0736 (15)	0.0366 (11)	0.0570 (14)	0.0078 (9)	−0.0211 (12)	0.0039 (10)
C10	0.0405 (10)	0.0417 (11)	0.0397 (10)	0.0017 (8)	−0.0059 (9)	0.0024 (8)
C11	0.0523 (11)	0.0496 (12)	0.0501 (12)	0.0022 (9)	0.0080 (11)	−0.0004 (10)
C12	0.0783 (16)	0.0509 (12)	0.0447 (12)	0.0132 (12)	0.0045 (12)	−0.0045 (11)
C13	0.0818 (17)	0.0480 (12)	0.0500 (13)	0.0058 (11)	−0.0209 (13)	−0.0055 (11)
C14	0.0621 (14)	0.0556 (14)	0.0693 (16)	−0.0098 (11)	−0.0195 (14)	0.0004 (12)
C15	0.0453 (11)	0.0587 (13)	0.0464 (12)	−0.0024 (10)	−0.0031 (10)	0.0035 (10)
N1	0.0593 (11)	0.0359 (9)	0.0465 (9)	0.0005 (8)	−0.0100 (8)	0.0014 (8)
O1	0.0640 (11)	0.0413 (8)	0.0582 (11)	−0.0047 (6)	−0.0065 (8)	0.0027 (7)
O2	0.0456 (8)	0.0486 (8)	0.0546 (9)	0.0083 (6)	0.0023 (7)	0.0085 (7)

Geometric parameters (Å, º) top

C2—O1	1.237 (2)	C8—C9	1.518 (3)
C2—N1	1.332 (3)	C8—H8A	0.9700
C2—C3	1.511 (3)	C8—H8B	0.9700
C3—C4	1.508 (3)	C9—N1	1.458 (3)
C3—H3A	0.9700	C9—H9A	0.9700
C3—H3B	0.9700	C9—H9B	0.9700
C4—C5	1.542 (3)	C10—C11	1.385 (3)
C4—H4A	0.9700	C10—C15	1.388 (3)
C4—H4B	0.9700	C11—C12	1.380 (3)
C5—N1	1.457 (3)	C11—H11	0.9300
C5—C6	1.530 (3)	C12—C13	1.380 (4)
C5—H5	0.9800	C12—H12	0.9300
C6—O2	1.414 (2)	C13—C14	1.364 (4)
C6—C7	1.540 (3)	C13—H13	0.9300
C6—H6	0.9800	C14—C15	1.388 (3)
C7—C10	1.510 (3)	C14—H14	0.9300
C7—C8	1.533 (3)	C15—H15	0.9300
C7—H7	0.9800	O2—H2	0.8200

O1—C2—N1	125.78 (19)	C9—C8—H8A	109.4
O1—C2—C3	125.9 (2)	C7—C8—H8A	109.4
N1—C2—C3	108.33 (17)	C9—C8—H8B	109.4
C2—C3—C4	106.09 (18)	C7—C8—H8B	109.4
C2—C3—H3A	110.5	H8A—C8—H8B	108.0
C4—C3—H3A	110.5	N1—C9—C8	109.40 (16)
C2—C3—H3B	110.5	N1—C9—H9A	109.8
C4—C3—H3B	110.5	C8—C9—H9A	109.8
H3A—C3—H3B	108.7	N1—C9—H9B	109.8
C3—C4—C5	106.18 (18)	C8—C9—H9B	109.8
C3—C4—H4A	110.5	H9A—C9—H9B	108.2
C5—C4—H4A	110.5	C11—C10—C15	117.7 (2)
C3—C4—H4B	110.5	C11—C10—C7	122.92 (19)
C5—C4—H4B	110.5	C15—C10—C7	119.4 (2)
H4A—C4—H4B	108.7	C10—C11—C12	121.4 (2)
N1—C5—C6	109.98 (17)	C10—C11—H11	119.3
N1—C5—C4	103.63 (18)	C12—C11—H11	119.3
C6—C5—C4	116.45 (19)	C13—C12—C11	120.0 (2)
N1—C5—H5	108.8	C13—C12—H12	120.0
C6—C5—H5	108.8	C11—C12—H12	120.0
C4—C5—H5	108.8	C14—C13—C12	119.7 (2)
O2—C6—C5	111.15 (17)	C14—C13—H13	120.2
O2—C6—C7	109.59 (16)	C12—C13—H13	120.2
C5—C6—C7	109.49 (16)	C13—C14—C15	120.3 (2)
O2—C6—H6	108.9	C13—C14—H14	119.9
C5—C6—H6	108.9	C15—C14—H14	119.9
C7—C6—H6	108.9	C10—C15—C14	121.0 (2)
C10—C7—C6	113.12 (15)	C10—C15—H15	119.5
C10—C7—C8	113.31 (18)	C14—C15—H15	119.5
C6—C7—C8	109.48 (17)	C2—N1—C5	115.52 (17)
C10—C7—H7	106.8	C2—N1—C9	125.54 (18)
C6—C7—H7	106.8	C5—N1—C9	118.92 (18)
C8—C7—H7	106.8	C6—O2—H2	109.5
C9—C8—C7	111.1 (2)

O1—C2—C3—C4	−175.3 (2)	C8—C7—C10—C15	139.5 (2)
N1—C2—C3—C4	5.1 (2)	C15—C10—C11—C12	−0.3 (3)
C2—C3—C4—C5	−4.7 (2)	C7—C10—C11—C12	179.3 (2)
C3—C4—C5—N1	2.8 (2)	C10—C11—C12—C13	−0.1 (4)
C3—C4—C5—C6	−118.0 (2)	C11—C12—C13—C14	0.7 (4)
N1—C5—C6—O2	−67.5 (2)	C12—C13—C14—C15	−1.0 (4)
C4—C5—C6—O2	50.0 (2)	C11—C10—C15—C14	0.0 (3)
N1—C5—C6—C7	53.7 (2)	C7—C10—C15—C14	−179.6 (2)
C4—C5—C6—C7	171.18 (18)	C13—C14—C15—C10	0.6 (3)
O2—C6—C7—C10	−63.7 (2)	O1—C2—N1—C5	176.9 (2)
C5—C6—C7—C10	174.18 (17)	C3—C2—N1—C5	−3.5 (2)
O2—C6—C7—C8	63.7 (2)	O1—C2—N1—C9	−4.6 (3)
C5—C6—C7—C8	−58.4 (2)	C3—C2—N1—C9	175.0 (2)
C10—C7—C8—C9	−174.06 (18)	C6—C5—N1—C2	125.53 (19)
C6—C7—C8—C9	58.6 (2)	C4—C5—N1—C2	0.4 (2)
C7—C8—C9—N1	−52.9 (3)	C6—C5—N1—C9	−53.1 (3)
C6—C7—C10—C11	85.3 (2)	C4—C5—N1—C9	−178.2 (2)
C8—C7—C10—C11	−40.0 (3)	C8—C9—N1—C2	−126.4 (2)
C6—C7—C10—C15	−95.1 (2)	C8—C9—N1—C5	52.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱ	0.82	2.00	2.807 (2)	170

Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₇NO₂
M_r	231.29
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	298
a, b, c (Å)	11.4164 (3), 6.6372 (2), 15.5118 (4)
V (Å³)	1175.38 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.60 × 0.56 × 0.13

Data collection
Diffractometer	Oxford Diffraction Gemini R CCD diffractometer
Absorption correction	Analytical (Clark & Reid, 1995)
T_min, T_max	0.901, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	26298, 1632, 1128
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.692

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.101, 1.03
No. of reflections	1632
No. of parameters	157
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.12

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2001), enCIFer (Allen et al., 2004).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱ	0.82	2.00	2.807 (2)	169.9

Symmetry code: (i) x, y+1, z.

Acknowledgements

The authors thank the Grant Agency of the Slovak Republic (grant Nos. 1/0161/08 and 1/0817/08) and Structural Funds, Interreg IIIA, for financial support in purchasing the diffractometer, and the Development Agency under contract No. APVV-0210-07.

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