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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 10| October 2012| Page o2857
https://doi.org/10.1107/S160053681203694X

3-Methyl­amino-3-phenyl­propan-1-ol

Wolfgang Frey,a Mohammad M. Ibrahim,b Basem F. Alib and Volker Jägera*

aUniversität Stuttgart, Institut für Organische Chemie, Pfaffenwaldring 55, D-70569 Stuttgart, Germany, and bDepartment of Chemistry, Al al-Bayt University, Mafraq 25113, Jordan
*Correspondence e-mail: jager.ioc@oc.uni-stuttgart.de

(Received 17 June 2012; accepted 27 August 2012; online 5 September 2012)

The title compound, C10H15NO, is an amino alcohol with the hy­droxy group residing on the terminal C atom. Apart from the hy­droxy group and the phenyl ring, all non-H atoms are almost coplanar. In the crystal, classical O—H⋯N and N—H⋯O hydrogen bonds connect the mol­ecules into centrosymmetric dimers [R22(12) descriptor] and tetra­meric units [R44(8) descriptor] as ring motifs, consolidating a three-dimensional network.

Related literature

For the syntheses of amino alcohols from isoxazolidines, isoxazolines and isoxazolinium salts, see: DeShong & Leginus, (1983[DeShong, P. & Leginus, J. M. (1983). J. Am. Chem. Soc. 105, 1686-1688.]); Henneböhle et al. (2004[Henneböhle, M., Le Roy, P.-Y., Hein, M., Ehrler, R. & Jäger, V. (2004). Z. Naturforsch. Teil B, 59, 451- 467.]); Ibrahim (2009[Ibrahim, M. M. (2009). Dissertation, Universität Stuttgart, Germany.]); Jäger & Buss, (1980[Jäger, V. & Buss, V. (1980). Liebigs Ann. Chem. pp. 101-121.]); Jäger et al. (1985[Jäger, V., Müller, I. & Paulus, E. F. (1985). Tetrahedron Lett. 26, 2997-3000.], 2010[Jäger, V., Frey, W., Bathich, Y., Shiva, S., Ibrahim, M., Henneböhle, M., LeRoy, P. Y. & Imerhasan, M. (2010). Z. Naturforsch. Teil B, 65b, 821-832.]); Jäger & Colinas (2002[Jäger, V. & Colinas, P. (2002). Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products, The Chemistry of Heterocyclic Compounds, edited by A. Padwa & W. H. Pearson, pp. 361-472. New York: Wiley.]); Lubell et al. (1991[Lubell, W. D., Kitamura, M. & Noyori, R. (1991). Tetrahedron Asymmetry, 2, 543-554.]). For hydrogen-bond motifs see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2 pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data

  • C10H15NO

  • Mr = 165.23

  • Monoclinic, P 21 /n

  • a = 5.9816 (8) Å

  • b = 23.8962 (19) Å

  • c = 7.4653 (8) Å

  • β = 111.119 (7)°

  • V = 995.40 (19) Å3

  • Z = 4

  • Cu Kα radiation

  • μ = 0.56 mm−1

  • T = 293 K

  • 0.80 × 0.50 × 0.20 mm
Data collection

  • Siemens P4 diffractometer

  • 3535 measured reflections

  • 1704 independent reflections

  • 896 reflections with I > 2σ(I)

  • Rint = 0.087

  • 3 standard reflections every 100 reflections intensity decay: 3%
Refinement

  • R[F2 > 2σ(F2)] = 0.071

  • wR(F2) = 0.201

  • S = 1.04

  • 1704 reflections

  • 119 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.22 e Å−3

  • Δρmin = −0.22 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1B⋯O1i 1.02 (4) 2.06 (3) 3.023 (4) 157 (2)
O1—H1A⋯N1ii 1.12 (4) 1.70 (4) 2.815 (3) 176 (3)
Symmetry codes: (i) x+1, y, z; (ii) -x+2, -y, -z+1.

Data collection: XSCANS (Bruker, 1996[Bruker (1996). XSCANS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: XP in SHELXTL-Plus.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053681203694X/im2389sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681203694X/im2389Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S160053681203694X/im2389Isup3.cml

checkCIF report


Comment top

Isoxazolidines, isoxazolines, and isoxazolinium salts are useful intermediates for syntheses of 1,3-amino alcohols by reduction with cleavage of the N–O bond (DeShong & Leginus, 1983; Jäger & Buss, 1980; Jäger et al., 1985; Jäger & Colinas, 2002; Henneböhle et al., 2004; Jäger et al., 2010). The structures and conformations of previously synthesized amino alcohols were all assigned on the basis of analytical as well as IR, 13C and 1H NMR data. When the 2-methyl-3-phenylisoxazolidine-3-carbonitrile was heated to reflux with lithium aluminium hydride in ether (abs.), the title compound I was formed in good yield. The starting isoxazolidine had been obtained from the corresponding N-methyl-isoxazolinium salt by cyanide addition (Henneböhle et al., 2004; Ibrahim, 2009; Jäger et al. 2010). The formation of the amino alcohol I was rationalized elsewhere (Ibrahim, 2009). The title compound I is already known from other routes (Lubell et al., 1991), yet, the crystal structure of I has not been published so far. We herein report the synthesis and the crystal structure of I, along with the supramolecular motifs present in the crystal lattice.

The asymmetric unit of I consists of one amino alcohol molecule with bond distances and angles in the normal range (Allen et al., 1987). The molecule, a primary alcohol and a secondary amine, adopts a planar zigzag-chain conformation (C1/C2/C3/N1/C4 almost coplanar), with both the hydroxy and the phenyl group being out-of-plane. The hydroxy and the phenyl group enclose dihedral angles of -60.3 (4)° and -63.0 (3)°, respectively, with the atoms of the carbon-chain (hydroxyl-O1/phenyl-C5-C1-C2-C3), see Fig. 1. In the crystal structure, molecules are hydrogen-bonded through the hydroxy groups as well as the amino groups (Table 1) giving rise to a three-dimensional network. The cooperative hydrogen bonds (alternating between hydroxy and amino groups) connect the molecules into chains down the crystallographic a axis (Fig. 2). These chains consist of alternating centrosymmetric dimers, with each dimer further interacting through the hydroxyl and amino groups with the adjacent one to form tetrameric units (Fig. 2). In terms of graph-set description, the hydrogen-bonded molecules might be described as forming two types of rings (Bernstein et al., 1995), the centrosymmetric dimers being R22(12) while R44(8) represents the descriptor for the tetramer units. These interactions consolidate a three-dimensional network.

This amino alcohol conformation in the crystal found here is in contrast to the conformations elucidated in solution on the basis of IR dilution experiments and extensive collections of 13C and 1H NMR data, notably coupling constants and substituent increments - there intramolecular hydrogen bonds O—H···N prevail to form monomers with chair-like arrangements (Jäger & Buss, 1980).

Related literature top

For the syntheses of amino alcohols from isoxazolidines, ioxazolines and isoxazolinium salts, see: DeShong & Leginus, (1983); Henneböhle et al. (2004); Ibrahim (2009); Jäger & Buss, (1980); Jäger et al. (1985, 2010); Jäger & Colinas (2002); Lubell et al. (1991). For hydrogen-bond motifs see: Bernstein et al. (1995). For standard bond lengths, see: Allen et al. (1987).

Experimental top

A solution of 2-methyl-3-phenylisoxazolidine-3-carbonitrile (150 mg, 0.80 mmol) in anhydrous diethylether (5 ml) at 0°C was added to a suspension of LiAlH4 (61.0 mg, 1.6 mmol, 2 eq) in anhydrous diethylether (15 ml) and stirred for 30 min. The mixture was allowed to warm up to room temperature and stirred for 1 h. The reaction mixture was then heated to reflux for 12 h. The solution was cooled to r.t., then at 0°C with vigorous stirring. H2O (0.5 ml), 5% NaOH (0.5 ml), and H2O (1.5 ml) were added sequentially. The reaction mixture was extracted with ether (4 x 15 ml) and CH2Cl2 (2 x 10 ml). The organic layers were dried over Na2SO4. The solvent was evaporated in vacuo (5 mbar, 40°C) to afford the amino alcohol I in analytically and spectroscopically pure form as a colorless solid [100 mg, 84%, m.p. 56–57°C; lit. 56–57°C (Lubell et al., 1991)]. Crystallization of the solid from ether afforded colorless crystals suitable for crystal structure determination. Analysis for C10H15NO, Calc.: C 72.69, H 9.15, N 8.48; Found: C 72.39, H 9.11, N 8.07.

Refinement top

Hydrogen atoms were located from the difference fourier map, but refined with fixed individual displacement parameters, using a riding model with d(C—H) ranging from 0.93 to 0.98 Å and Uiso(H) = 1.2 Ueq(C) or Uiso(H) = 1.5 Ueq(Cmethyl). In addition, the methyl group is allowed to rotate but not to tip. Hydrogen atoms attached to the hydroxy function and to the amino moiety are refined freely because of their relevance in hydrogen bonding.

Structure description top

Isoxazolidines, isoxazolines, and isoxazolinium salts are useful intermediates for syntheses of 1,3-amino alcohols by reduction with cleavage of the N–O bond (DeShong & Leginus, 1983; Jäger & Buss, 1980; Jäger et al., 1985; Jäger & Colinas, 2002; Henneböhle et al., 2004; Jäger et al., 2010). The structures and conformations of previously synthesized amino alcohols were all assigned on the basis of analytical as well as IR, 13C and 1H NMR data. When the 2-methyl-3-phenylisoxazolidine-3-carbonitrile was heated to reflux with lithium aluminium hydride in ether (abs.), the title compound I was formed in good yield. The starting isoxazolidine had been obtained from the corresponding N-methyl-isoxazolinium salt by cyanide addition (Henneböhle et al., 2004; Ibrahim, 2009; Jäger et al. 2010). The formation of the amino alcohol I was rationalized elsewhere (Ibrahim, 2009). The title compound I is already known from other routes (Lubell et al., 1991), yet, the crystal structure of I has not been published so far. We herein report the synthesis and the crystal structure of I, along with the supramolecular motifs present in the crystal lattice.

The asymmetric unit of I consists of one amino alcohol molecule with bond distances and angles in the normal range (Allen et al., 1987). The molecule, a primary alcohol and a secondary amine, adopts a planar zigzag-chain conformation (C1/C2/C3/N1/C4 almost coplanar), with both the hydroxy and the phenyl group being out-of-plane. The hydroxy and the phenyl group enclose dihedral angles of -60.3 (4)° and -63.0 (3)°, respectively, with the atoms of the carbon-chain (hydroxyl-O1/phenyl-C5-C1-C2-C3), see Fig. 1. In the crystal structure, molecules are hydrogen-bonded through the hydroxy groups as well as the amino groups (Table 1) giving rise to a three-dimensional network. The cooperative hydrogen bonds (alternating between hydroxy and amino groups) connect the molecules into chains down the crystallographic a axis (Fig. 2). These chains consist of alternating centrosymmetric dimers, with each dimer further interacting through the hydroxyl and amino groups with the adjacent one to form tetrameric units (Fig. 2). In terms of graph-set description, the hydrogen-bonded molecules might be described as forming two types of rings (Bernstein et al., 1995), the centrosymmetric dimers being R22(12) while R44(8) represents the descriptor for the tetramer units. These interactions consolidate a three-dimensional network.

This amino alcohol conformation in the crystal found here is in contrast to the conformations elucidated in solution on the basis of IR dilution experiments and extensive collections of 13C and 1H NMR data, notably coupling constants and substituent increments - there intramolecular hydrogen bonds O—H···N prevail to form monomers with chair-like arrangements (Jäger & Buss, 1980).

For the syntheses of amino alcohols from isoxazolidines, ioxazolines and isoxazolinium salts, see: DeShong & Leginus, (1983); Henneböhle et al. (2004); Ibrahim (2009); Jäger & Buss, (1980); Jäger et al. (1985, 2010); Jäger & Colinas (2002); Lubell et al. (1991). For hydrogen-bond motifs see: Bernstein et al. (1995). For standard bond lengths, see: Allen et al. (1987).

Computing details top

Data collection: XSCANS (Bruker, 1996); cell refinement: XSCANS (Bruker, 1996); data reduction: XSCANS (Bruker, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: XP in SHELXTL-Plus (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of I, with thermal ellipsoids drawn at the 30% probability level.
[Figure 2] Fig. 2. A view down c axis showing chains of hydrogen bonding molecules along a axis. The chains consist of alternating centrosymmetric dimers, with each dimer further interacting through the hydroxyl and amino groups with the adjacent one to form tetrameric units.
3-Methylamino-3-phenylpropan-1-ol top
Crystal data top
C10H15NOF(000) = 360
Mr = 165.23Dx = 1.103 Mg m−3
Monoclinic, P21/nCu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ynCell parameters from 30 reflections
a = 5.9816 (8) Åθ = 21.0–22.5°
b = 23.8962 (19) ŵ = 0.56 mm−1
c = 7.4653 (8) ÅT = 293 K
β = 111.119 (7)°Block, colourless
V = 995.40 (19) Å30.80 × 0.50 × 0.20 mm
Z = 4
Data collection top
Siemens P4
diffractometer		Rint = 0.087
Radiation source: fine-focus sealed tubeθmax = 67.5°, θmin = 3.7°
Graphite monochromatorh = −7→7
ω scansk = −28→28
3535 measured reflectionsl = −8→8
1704 independent reflections3 standard reflections every 100 reflections
896 reflections with I > 2σ(I) intensity decay: 3%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.071H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.201 w = 1/[σ2(Fo2) + (0.0232P)2 + 0.9564P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
1704 reflectionsΔρmax = 0.22 e Å−3
119 parametersΔρmin = −0.22 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.026 (2)
Crystal data top
C10H15NOV = 995.40 (19) Å3
Mr = 165.23Z = 4
Monoclinic, P21/nCu Kα radiation
a = 5.9816 (8) ŵ = 0.56 mm−1
b = 23.8962 (19) ÅT = 293 K
c = 7.4653 (8) Å0.80 × 0.50 × 0.20 mm
β = 111.119 (7)°
Data collection top
Siemens P4
diffractometer		Rint = 0.087
3535 measured reflections3 standard reflections every 100 reflections
1704 independent reflections intensity decay: 3%
896 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0710 restraints
wR(F2) = 0.201H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.22 e Å−3
1704 reflectionsΔρmin = −0.22 e Å−3
119 parameters
Special details top

Experimental. 1H NMR (500.2 MHz, MeOD): d = 1.82 (dddd, 3J1a,2a = 7.9 Hz, 3J1b,2a = 5.6 Hz, 2J2a,2b = 14.0 Hz, 3J2a,3 = 5.2 Hz, 1 H, 2-Ha), 2.06 (dddd, 3J1a,2b = 6.2 Hz, 3J1b,2b = 7.5 Hz, 2J2a,2b = 14.2 Hz, 3J2b,3 = 5.8 Hz, 1 H, 2-Hb), 2.18 (s, 3 H, NCH3), 3.42 (ddd, 2J1a,1b = 10.8 Hz, 3J1a,2a = 8.1 Hz, 3J1a,2b = 6.1 Hz, 1 H, 1-Ha), 3.49 (ddd, 2J1a,1b = 8.0 Hz, 3J1b,2a = 5.0 Hz, 3J1b,2b = 6.8 Hz, 1 H, 1-Hb), 3.65 (dd, 3J2a,3 = 8.3 Hz, 3J2b,3 = 6.0 Hz, 1 H, 3-H), 7.23-7.35 (m, 5 H, C6H5); 13C NMR (125.8 MHz, MeOD): d = 34.0 (q, NCH3), 40.7 (t, C-2), 60.4 (t, C-1), 63.7 (d, C-3), 128.2, 128.4, 129.6 (3 d, o-, m-, p-C of C6H5), 143.8 (s, i-C of C6H5).

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
xyzUiso*/Ueq
O10.6223 (4)0.02730 (9)0.2754 (3)0.0633 (7)
H1A0.622 (7)−0.0130 (18)0.351 (6)0.111 (14)*
N11.3595 (5)0.07300 (10)0.5221 (4)0.0610 (8)
H1B1.458 (6)0.0688 (12)0.436 (5)0.063 (9)*
C10.7636 (6)0.02462 (14)0.1583 (5)0.0639 (9)
H1C0.72080.05550.06810.077*
H1D0.7277−0.00990.08490.077*
C21.0300 (5)0.02701 (12)0.2739 (4)0.0564 (8)
H2A1.11680.02380.18680.068*
H2B1.0732−0.00490.35990.068*
C31.1102 (5)0.08083 (12)0.3929 (4)0.0565 (8)
H31.01210.08480.47270.068*
C41.4610 (8)0.11951 (15)0.6516 (6)0.0922 (14)
H4A1.46540.15220.57820.138*
H4B1.62070.11020.73510.138*
H4C1.36370.12680.72700.138*
C51.0643 (6)0.13176 (12)0.2623 (5)0.0603 (9)
C60.8826 (7)0.16881 (14)0.2513 (6)0.0790 (11)
H60.79480.16400.33070.095*
C70.8291 (8)0.21376 (16)0.1211 (7)0.0936 (14)
H70.70720.23870.11520.112*
C80.9553 (9)0.22067 (16)0.0047 (7)0.0925 (14)
H80.91670.2496−0.08440.111*
C91.1390 (8)0.18531 (15)0.0176 (6)0.0851 (12)
H91.22920.1911−0.05950.102*
C101.1927 (7)0.14055 (14)0.1451 (5)0.0737 (10)
H101.31690.11630.15110.088*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0526 (13)0.0690 (14)0.0665 (15)0.0047 (10)0.0194 (11)0.0030 (11)
N10.0552 (15)0.0620 (16)0.0583 (17)−0.0054 (12)0.0114 (14)−0.0037 (12)
C10.0563 (18)0.075 (2)0.0562 (19)−0.0061 (15)0.0158 (16)−0.0016 (15)
C20.0557 (17)0.0585 (17)0.0554 (18)−0.0043 (13)0.0206 (15)−0.0044 (13)
C30.0547 (17)0.0579 (17)0.0563 (19)0.0004 (13)0.0193 (16)−0.0015 (13)
C40.101 (3)0.071 (2)0.079 (3)−0.015 (2)0.001 (2)−0.0142 (19)
C50.0563 (18)0.0562 (17)0.063 (2)0.0016 (14)0.0145 (16)0.0007 (14)
C60.078 (2)0.066 (2)0.092 (3)0.0102 (17)0.030 (2)−0.0017 (19)
C70.090 (3)0.065 (2)0.109 (4)0.021 (2)0.016 (3)0.005 (2)
C80.114 (3)0.067 (2)0.082 (3)0.009 (2)0.019 (3)0.011 (2)
C90.106 (3)0.071 (2)0.084 (3)−0.001 (2)0.040 (3)0.0100 (19)
C100.082 (2)0.068 (2)0.073 (2)0.0038 (17)0.031 (2)0.0077 (17)
Geometric parameters (Å, º) top
O1—C11.420 (4)C4—H4B0.9600
O1—H1A1.12 (4)C4—H4C0.9600
N1—C41.454 (4)C5—C101.373 (5)
N1—C31.468 (4)C5—C61.381 (4)
N1—H1B1.02 (4)C6—C71.406 (5)
C1—C21.516 (4)C6—H60.9300
C1—H1C0.9700C7—C81.351 (6)
C1—H1D0.9700C7—H70.9300
C2—C31.538 (4)C8—C91.362 (6)
C2—H2A0.9700C8—H80.9300
C2—H2B0.9700C9—C101.390 (5)
C3—C51.521 (4)C9—H90.9300
C3—H30.9800C10—H100.9300
C4—H4A0.9600
C1—O1—H1A112 (2)N1—C4—H4B109.5
C4—N1—C3114.9 (3)H4A—C4—H4B109.5
C4—N1—H1B107.1 (17)N1—C4—H4C109.5
C3—N1—H1B106.3 (18)H4A—C4—H4C109.5
O1—C1—C2112.6 (3)H4B—C4—H4C109.5
O1—C1—H1C109.1C10—C5—C6118.2 (3)
C2—C1—H1C109.1C10—C5—C3121.2 (3)
O1—C1—H1D109.1C6—C5—C3120.5 (3)
C2—C1—H1D109.1C5—C6—C7120.6 (4)
H1C—C1—H1D107.8C5—C6—H6119.7
C1—C2—C3113.9 (3)C7—C6—H6119.7
C1—C2—H2A108.8C8—C7—C6119.8 (4)
C3—C2—H2A108.8C8—C7—H7120.1
C1—C2—H2B108.8C6—C7—H7120.1
C3—C2—H2B108.8C7—C8—C9120.2 (4)
H2A—C2—H2B107.7C7—C8—H8119.9
N1—C3—C5115.4 (2)C9—C8—H8119.9
N1—C3—C2107.7 (2)C8—C9—C10120.5 (4)
C5—C3—C2110.6 (2)C8—C9—H9119.8
N1—C3—H3107.6C10—C9—H9119.8
C5—C3—H3107.6C5—C10—C9120.7 (4)
C2—C3—H3107.6C5—C10—H10119.7
N1—C4—H4A109.5C9—C10—H10119.7
O1—C1—C2—C3−60.3 (4)C10—C5—C6—C70.9 (5)
C4—N1—C3—C558.3 (4)C3—C5—C6—C7−175.6 (3)
C4—N1—C3—C2−177.6 (3)C5—C6—C7—C80.4 (6)
C1—C2—C3—N1169.9 (3)C6—C7—C8—C9−2.1 (7)
C1—C2—C3—C5−63.0 (3)C7—C8—C9—C102.5 (7)
N1—C3—C5—C1054.1 (4)C6—C5—C10—C9−0.6 (5)
C2—C3—C5—C10−68.5 (4)C3—C5—C10—C9175.9 (3)
N1—C3—C5—C6−129.5 (3)C8—C9—C10—C5−1.1 (6)
C2—C3—C5—C6107.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···O1i1.02 (4)2.06 (3)3.023 (4)157 (2)
O1—H1A···N1ii1.12 (4)1.70 (4)2.815 (3)176 (3)
Symmetry codes: (i) x+1, y, z; (ii) −x+2, −y, −z+1.

Experimental details

Crystal data
Chemical formulaC10H15NO
Mr165.23
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)5.9816 (8), 23.8962 (19), 7.4653 (8)
β (°) 111.119 (7)
V (Å3)995.40 (19)
Z4
Radiation typeCu Kα
µ (mm−1)0.56
Crystal size (mm)0.80 × 0.50 × 0.20
Data collection
DiffractometerSiemens P4
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		3535, 1704, 896
Rint0.087
(sin θ/λ)max (Å−1)0.599
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.071, 0.201, 1.04
No. of reflections1704
No. of parameters119
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.22, −0.22

Computer programs: XSCANS (Bruker, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL-Plus (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···O1i1.02 (4)2.06 (3)3.023 (4)157 (2)
O1—H1A···N1ii1.12 (4)1.70 (4)2.815 (3)176 (3)
Symmetry codes: (i) x+1, y, z; (ii) −x+2, −y, −z+1.
 

Acknowledgements

We thank the German Academic Exchange Service (DAAD) for PhD scholarship to MMI.

References

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 First citationJäger, V., Frey, W., Bathich, Y., Shiva, S., Ibrahim, M., Henneböhle, M., LeRoy, P. Y. & Imerhasan, M. (2010). Z. Naturforsch. Teil B, 65b, 821–832.  Google Scholar
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ISSN: 2056-9890
Volume 68| Part 10| October 2012| Page o2857
https://doi.org/10.1107/S160053681203694X
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