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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 7| July 2012| Pages o2275-o2276
https://doi.org/10.1107/S1600536812028838

4-{[4-(Hy­dr­oxy­meth­yl)piperidin-1-yl]meth­yl}phenol

M. C. R. Simões,a I. M. R. Landre,b M. S. Moreira,a C. Viegas Jra and A. C. Doriguettob*

aLaboratório de Fitoquímica e Química Medicinal, Instituto de Química, Universidade Federal de Alfenas (UNIFAL–MG), Alfenas, MG, Brazil, and bLaboratório de Cristalografia, Instituto de Química, Universidade Federal de Alfenas (UNIFAL–MG), Alfenas, MG, Brazil
*Correspondence e-mail: doriguetto@unifal-mg.edu.br

(Received 4 June 2012; accepted 25 June 2012; online 30 June 2012)

In the title compound, C13H19NO2, the piperidine ring has a chair conformation with the exocyclic N—C bond in an equatorial position. In the crystal, mol­ecules are linked head-to-tail by phenol O—H⋯O hydrogen bonds to hy­droxy­methyl­ene O-atom acceptors, forming chains which extend along [100]. These chains form two-dimensional networks lying parallel to (101) through cyclic hydrogen-bonding associations [graph set R44(30)], involving hy­droxy O—H donors and piperidine N-atom acceptors.

Related literature

For preparative procedures of the title compound and related compounds, see: Kulagowski et al. (1996[Kulagowski, J. J., Broughton, H. B., Curtis, N. R., Mawer, I. A., Ridgill, M. P., Baker, R., Emms, F., Freedman, S. B., Marwood, R., Patel, S., Patel, S., Ragan, C. I. & Leeson, P. D. (1996). J. Med. Chem. 39, 1941-1942.]); Schepartz & Breslow (1987)[Schepartz, A. & Breslow, R. (1987) J. Am. Chem. Soc. 109, 1814-1826.]; Menegatti et al. (2003[Menegatti, R., Cunha, C. A., Ferreira, F. V., Perreira, R. F. E., El-Nabawi, A., Eldefrawi, T. A., Albuquerque, X. E., Neves, G., Rates, K. M. S., Fraga, M. A. C. & Barreiro, J. E. (2003). Bioorg. Med. Chem. 11, 4807-4813.]). For physiological properties of these compounds, see: Menegatti et al. (2003[Menegatti, R., Cunha, C. A., Ferreira, F. V., Perreira, R. F. E., El-Nabawi, A., Eldefrawi, T. A., Albuquerque, X. E., Neves, G., Rates, K. M. S., Fraga, M. A. C. & Barreiro, J. E. (2003). Bioorg. Med. Chem. 11, 4807-4813.]); Romero et al. (2003[Romero, S. A. L., Fraga, M. A. C. & Barreiro, J. E. (2003). Quim. Nova, 26, 347-358.]). For ring conformations, see: Domenicano et al. (1975[Domenicano, A., Vaciago, A. & Coulson, C. A. (1975). Acta Cryst. B31, 221-234.]). For graph-set analysis, see: Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]).

[Scheme 1]

Experimental

Crystal data

  • C13H19NO2

  • Mr = 221.29

  • Monoclinic, C c

  • a = 6.0428 (2) Å

  • b = 17.2269 (7) Å

  • c = 11.3010 (4) Å

  • β = 94.663 (4)°

  • V = 1172.53 (7) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 150 K

  • 0.64 × 0.15 × 0.07 mm
Data collection

  • Oxford Diffraction Xcalibur Atlas Gemini Ultra CCD diffractometer

  • 5289 measured reflections

  • 1474 independent reflections

  • 1326 reflections with I > 2σ(I)

  • Rint = 0.021
Refinement

  • R[F2 > 2σ(F2)] = 0.033

  • wR(F2) = 0.084

  • S = 1.08

  • 1474 reflections

  • 151 parameters

  • 2 restraints

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

  • Δρmax = 0.23 e Å−3

  • Δρmin = −0.16 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1⋯N1i 0.78 (3) 2.04 (3) 2.813 (2) 174 (3)
O2—H2⋯O1ii 0.89 (2) 1.82 (2) 2.702 (2) 176 (2)
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) x, y, z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2004 (Burla et al., 2005[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812028838/zs2215sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812028838/zs2215Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812028838/zs2215Isup3.cml

checkCIF report


Comment top

A wide range of benzylpiperazine and benzylpiperidine derivatives are reported in the literature as products or intermediates in the synthesis of new compound prototypes (Kulagowski et al., 1996) showing various biological activities, including antipsychotic (Menegatti et al., 2003) and antidepressant properties (Romero et al., 2003). These compounds can be obtained by the reaction of aldehydes or ketones with primary and secondary amines using a reducing agent. In this context, the title compound 4-((4-(hydroxymethyl)piperidin-1-yl)methyl)phenol, C13H19NO2 was prepared from 4-hydroxybenzaldehyde and 4-piperidinemethanol (Menegatti et al., 2003; Schepartz & Breslow, 1987) with a 96% yield. In this compound (Fig. 1) the mean plane through the C7 and phenolic atoms shows that this moiety is, as expected, planar (r.m.s deviation = 0.0121 Å). Considering the non-H atoms, the largest deviation from the least-squares plane is 0.021 (1) Å for C7. The H2 atom deviates -0.23 (2) Å from the least-squares plane due to its involvement in intermolecular H bonds. The least-squares planes through atoms C3—C4—N1—C7—C8 [r.m.s = 0.0149 Å and largest deviation = 0.019 (1) Å for C4] and C6—C5—N1—C7 [r.m.s. =0.0233 Å and largest deviation = 0.0243 (8) Å for C5], show that these moieties are also individually very planar and form dihedral angles of 77.38 (9) and 76.65 (7)° with the phenolic ring. The piperidine ring has a chair conformation with a weighted average absolute torsion angle of 56.85(6,52)° (1st is the e.s.d. internal and 2nd is the external one) (Domenicano et al., 1975). Considering the two possible chair conformations of piperidine rings, the N1—C7 bond is an equatorial orientation.

There are two independent classic hydrogen-bond types involving the phenolic, hydroxymethylene and piperidine groups, contributing to the stability of the crystal packing (Table 1). Translation-related molecules are linked head-to-tail along [001] through phenolic O—H···O hydrogen bonds to hydroxymethylene O-atom acceptors (Fig. 2). This hydroxy group also acts as a donor to the piperidine nitrogen (Fig. 3), forming two-dimensional sheets which extend across (010). The morphology of the cyclic H-bond pattern within the sheets is R44(30) (Etter et al., 1990). No π-π interactions are present in the structure.

Related literature top

For preparative procedures of the title compound and related compounds, see: Kulagowski et al. (1996); Schepartz & Breslow (1987); Menegatti et al. (2003). For physiological properties of these compounds, see: Menegatti et al. (2003); Romero et al. (2003). For ring conformations, see: Domenicano et al. (1975). For graph-set analysis, see: Etter et al. (1990).

Experimental top

4-Hydroxybenzaldehyde (0.3 g) and 4-piperidinemethanol (0.27 g) were dissolved in 8.5 mL of methanol. The pH was adjusted to 5 with the addition of acetic acid before the addition of 0.15 g of sodium cyanoborohydride. The system was kept stirred under reflux for 5 h, followed by addition of concentrated HCl (ca. 2 mL) to pH 2.0 and the resulting solution was then basified to pH 12 with solid NaOH. The reaction mixture was extracted with chloroform (3 x 15 mL), and the combined organic phase was subsequently washed with water, then brine, dried over anhydrous sodium sulfate, followed by filtration. However, it was observed that the product was present mainly in the aqueous layer and after a slow evaporation of the solvent, crystalline material (m.p. 329 K) suitable for X-ray diffraction formed. IR (KBr, cm-1): ν 3444, 2334, 1573, 1413, and 1012.

Refinement top

Positional and anisotropic displacement parameters were refined for all non-H atoms. The H atoms of the aromatic and aliphatic groups were positioned stereochemically and were refined with fixed individual displacement parameters [Uiso(H) = 1.2Ueq(C)] using a riding model with C—H(aromatic) = 0.95 Å and C—H(aliphatic) = 0.99 Å. The hydroxyl H atoms were located by difference-Fourier synthesis and were set as isotropic [Uiso(H) = 1.5Ueq(O)]. In the absence of significant anomalous scattering, the Friedel pair reflections were merged before the final refinement.

Structure description top

A wide range of benzylpiperazine and benzylpiperidine derivatives are reported in the literature as products or intermediates in the synthesis of new compound prototypes (Kulagowski et al., 1996) showing various biological activities, including antipsychotic (Menegatti et al., 2003) and antidepressant properties (Romero et al., 2003). These compounds can be obtained by the reaction of aldehydes or ketones with primary and secondary amines using a reducing agent. In this context, the title compound 4-((4-(hydroxymethyl)piperidin-1-yl)methyl)phenol, C13H19NO2 was prepared from 4-hydroxybenzaldehyde and 4-piperidinemethanol (Menegatti et al., 2003; Schepartz & Breslow, 1987) with a 96% yield. In this compound (Fig. 1) the mean plane through the C7 and phenolic atoms shows that this moiety is, as expected, planar (r.m.s deviation = 0.0121 Å). Considering the non-H atoms, the largest deviation from the least-squares plane is 0.021 (1) Å for C7. The H2 atom deviates -0.23 (2) Å from the least-squares plane due to its involvement in intermolecular H bonds. The least-squares planes through atoms C3—C4—N1—C7—C8 [r.m.s = 0.0149 Å and largest deviation = 0.019 (1) Å for C4] and C6—C5—N1—C7 [r.m.s. =0.0233 Å and largest deviation = 0.0243 (8) Å for C5], show that these moieties are also individually very planar and form dihedral angles of 77.38 (9) and 76.65 (7)° with the phenolic ring. The piperidine ring has a chair conformation with a weighted average absolute torsion angle of 56.85(6,52)° (1st is the e.s.d. internal and 2nd is the external one) (Domenicano et al., 1975). Considering the two possible chair conformations of piperidine rings, the N1—C7 bond is an equatorial orientation.

There are two independent classic hydrogen-bond types involving the phenolic, hydroxymethylene and piperidine groups, contributing to the stability of the crystal packing (Table 1). Translation-related molecules are linked head-to-tail along [001] through phenolic O—H···O hydrogen bonds to hydroxymethylene O-atom acceptors (Fig. 2). This hydroxy group also acts as a donor to the piperidine nitrogen (Fig. 3), forming two-dimensional sheets which extend across (010). The morphology of the cyclic H-bond pattern within the sheets is R44(30) (Etter et al., 1990). No π-π interactions are present in the structure.

For preparative procedures of the title compound and related compounds, see: Kulagowski et al. (1996); Schepartz & Breslow (1987); Menegatti et al. (2003). For physiological properties of these compounds, see: Menegatti et al. (2003); Romero et al. (2003). For ring conformations, see: Domenicano et al. (1975). For graph-set analysis, see: Etter et al. (1990).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. Molecular conformation and atom-numbering scheme for the title compound. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.
[Figure 2] Fig. 2. The crystal packing of (I) showing the chains formed along [001]. Hydrogen bonds are shown as dashed lines. [For symmetry codes (i) and (ii), see Table 1. For other codes: (iii) x, y, z - 1; (iv) x - 1/2, -y + 1/2, z + 1/2; (v) x - 1/2, -y + 1/2, z - 1/2].
[Figure 3] Fig. 3. The crystal packing showing the chain extension formed along [101]. Hydrogen bonds are shown as dashed lines. [For symmetry codes (i) and (v), see Table 1 and Fig. 1. For other codes: (vi) x - 1, y, z - 1; (vii) x + 1, y, z + 1; (viii) x + 3/2, -y + 1/2, z + 3/2].
4-{[4-(Hydroxymethyl)piperidin-1-yl]methyl}phenol top
Crystal data top
C13H19NO2F(000) = 480
Mr = 221.29Dx = 1.254 Mg m−3
Monoclinic, CcMelting point: 329 K
Hall symbol: C -2ycMo Kα radiation, λ = 0.71073 Å
a = 6.0428 (2) ÅCell parameters from 3165 reflections
b = 17.2269 (7) Åθ = 3.0–29.4°
c = 11.3010 (4) ŵ = 0.08 mm−1
β = 94.663 (4)°T = 150 K
V = 1172.53 (7) Å3Prism, colourless
Z = 40.64 × 0.15 × 0.07 mm
Data collection top
Oxford Diffraction Xcalibur Atlas Gemini Ultra CCD
diffractometer		1326 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray SourceRint = 0.021
Graphite monochromatorθmax = 29.5°, θmin = 3.0°
Detector resolution: 10.4186 pixels mm-1h = −8→7
ω scansk = −23→21
5289 measured reflectionsl = −14→15
1474 independent reflections
Refinement top
Refinement on F22 restraints
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.033 w = 1/[σ2(Fo2) + (0.0533P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.084(Δ/σ)max < 0.001
S = 1.08Δρmax = 0.23 e Å−3
1474 reflectionsΔρmin = −0.16 e Å−3
151 parameters
Crystal data top
C13H19NO2V = 1172.53 (7) Å3
Mr = 221.29Z = 4
Monoclinic, CcMo Kα radiation
a = 6.0428 (2) ŵ = 0.08 mm−1
b = 17.2269 (7) ÅT = 150 K
c = 11.3010 (4) Å0.64 × 0.15 × 0.07 mm
β = 94.663 (4)°
Data collection top
Oxford Diffraction Xcalibur Atlas Gemini Ultra CCD
diffractometer		1326 reflections with I > 2σ(I)
5289 measured reflectionsRint = 0.021
1474 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0332 restraints
wR(F2) = 0.084H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 0.23 e Å−3
1474 reflectionsΔρmin = −0.16 e Å−3
151 parameters
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
O1−0.0007 (2)0.24016 (8)0.46384 (12)0.0261 (3)
O2−0.1558 (2)0.11336 (9)1.34326 (13)0.0288 (3)
N10.3345 (2)0.12022 (8)0.86219 (13)0.0188 (3)
C70.3394 (3)0.05377 (11)0.94654 (16)0.0240 (4)
H7A0.49560.04240.97430.029*
H7B0.27790.00730.90410.029*
C20.2291 (3)0.17910 (11)0.61963 (15)0.0194 (4)
H2A0.16770.13020.58230.023*
C10.2165 (3)0.24167 (10)0.52460 (17)0.0230 (4)
H1A0.24550.29320.56140.028*
H1B0.32990.2320.46780.028*
C90.0023 (3)0.03522 (10)1.06266 (17)0.0245 (4)
H9−0.05840.00151.00190.029*
C80.2102 (3)0.06858 (10)1.05249 (15)0.0216 (4)
C60.0905 (3)0.19913 (10)0.72254 (16)0.0200 (4)
H6A0.14480.24840.75960.024*
H6B−0.06620.20670.6920.024*
C120.1777 (3)0.13204 (10)1.24159 (16)0.0232 (4)
H120.240.16481.30320.028*
C10−0.1178 (3)0.05027 (11)1.15973 (17)0.0245 (4)
H10−0.25920.02691.16480.029*
C50.1038 (3)0.13527 (10)0.81530 (15)0.0201 (4)
H5A0.0150.15040.88150.024*
H5B0.03910.08710.77960.024*
C130.2946 (3)0.11669 (10)1.14421 (16)0.0235 (4)
H130.43660.13961.13970.028*
C30.4675 (3)0.16258 (11)0.66953 (17)0.0239 (4)
H3A0.55690.14570.60460.029*
H3B0.53480.21060.70450.029*
C11−0.0317 (3)0.09943 (10)1.24953 (16)0.0221 (4)
C40.4701 (3)0.09956 (11)0.76403 (16)0.0227 (4)
H4A0.41310.05060.7270.027*
H4B0.62510.09040.79630.027*
H1−0.038 (4)0.2801 (15)0.437 (2)0.034*
H2−0.106 (4)0.1540 (14)1.386 (2)0.034*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0303 (7)0.0222 (6)0.0243 (7)0.0004 (6)−0.0057 (6)0.0034 (5)
O20.0317 (7)0.0280 (7)0.0271 (7)−0.0054 (6)0.0058 (6)0.0010 (6)
N10.0180 (7)0.0199 (7)0.0180 (7)0.0020 (6)−0.0014 (6)−0.0029 (5)
C70.0284 (10)0.0193 (8)0.0234 (9)0.0037 (7)−0.0040 (8)−0.0005 (7)
C20.0192 (9)0.0208 (8)0.0181 (8)−0.0012 (7)0.0008 (7)−0.0018 (7)
C10.0231 (9)0.0238 (9)0.0223 (9)−0.0021 (7)0.0027 (7)−0.0015 (7)
C90.0294 (10)0.0190 (8)0.0236 (9)0.0004 (8)−0.0070 (8)0.0002 (7)
C80.0259 (9)0.0174 (8)0.0207 (9)0.0032 (7)−0.0029 (7)0.0020 (6)
C60.0154 (8)0.0216 (8)0.0227 (8)0.0028 (7)0.0003 (7)0.0004 (7)
C120.0269 (9)0.0198 (8)0.0218 (9)−0.0028 (7)−0.0038 (7)−0.0014 (7)
C100.0241 (9)0.0203 (9)0.0281 (10)−0.0023 (7)−0.0034 (8)0.0061 (7)
C50.0166 (8)0.0228 (9)0.0208 (9)0.0017 (7)0.0007 (7)−0.0013 (7)
C130.0234 (10)0.0215 (9)0.0251 (9)−0.0032 (7)−0.0017 (7)0.0020 (7)
C30.0181 (9)0.0299 (10)0.0239 (9)−0.0001 (7)0.0026 (7)−0.0046 (8)
C110.0253 (9)0.0196 (8)0.0209 (9)0.0021 (8)−0.0004 (7)0.0058 (7)
C40.0181 (8)0.0273 (9)0.0223 (9)0.0053 (8)−0.0003 (7)−0.0058 (7)
Geometric parameters (Å, º) top
O1—C11.431 (2)C9—H90.95
O1—H10.78 (3)C8—C131.391 (2)
O2—C111.368 (2)C6—C51.517 (2)
O2—H20.89 (2)C6—H6A0.99
N1—C51.474 (2)C6—H6B0.99
N1—C41.475 (2)C12—C131.380 (3)
N1—C71.488 (2)C12—C111.394 (3)
C7—C81.503 (3)C12—H120.95
C7—H7A0.99C10—C111.390 (3)
C7—H7B0.99C10—H100.95
C2—C11.519 (3)C5—H5A0.99
C2—C61.527 (2)C5—H5B0.99
C2—C31.531 (2)C13—H130.95
C2—H2A1C3—C41.522 (3)
C1—H1A0.99C3—H3A0.99
C1—H1B0.99C3—H3B0.99
C9—C101.388 (3)C4—H4A0.99
C9—C81.395 (3)C4—H4B0.99
C1—O1—H1113.4 (19)C2—C6—H6B109.4
C11—O2—H2111.9 (16)H6A—C6—H6B108
C5—N1—C4109.81 (13)C13—C12—C11120.00 (17)
C5—N1—C7109.54 (14)C13—C12—H12120
C4—N1—C7108.23 (13)C11—C12—H12120
N1—C7—C8113.27 (14)C9—C10—C11120.13 (17)
N1—C7—H7A108.9C9—C10—H10119.9
C8—C7—H7A108.9C11—C10—H10119.9
N1—C7—H7B108.9N1—C5—C6111.80 (14)
C8—C7—H7B108.9N1—C5—H5A109.3
H7A—C7—H7B107.7C6—C5—H5A109.3
C1—C2—C6112.29 (15)N1—C5—H5B109.3
C1—C2—C3112.57 (15)C6—C5—H5B109.3
C6—C2—C3108.63 (13)H5A—C5—H5B107.9
C1—C2—H2A107.7C12—C13—C8121.87 (17)
C6—C2—H2A107.7C12—C13—H13119.1
C3—C2—H2A107.7C8—C13—H13119.1
O1—C1—C2108.50 (14)C4—C3—C2110.28 (15)
O1—C1—H1A110C4—C3—H3A109.6
C2—C1—H1A110C2—C3—H3A109.6
O1—C1—H1B110C4—C3—H3B109.6
C2—C1—H1B110C2—C3—H3B109.6
H1A—C1—H1B108.4H3A—C3—H3B108.1
C10—C9—C8121.37 (16)O2—C11—C10118.44 (17)
C10—C9—H9119.3O2—C11—C12122.46 (17)
C8—C9—H9119.3C10—C11—C12119.10 (17)
C13—C8—C9117.51 (17)N1—C4—C3112.40 (14)
C13—C8—C7120.81 (16)N1—C4—H4A109.1
C9—C8—C7121.68 (16)C3—C4—H4A109.1
C5—C6—C2111.16 (14)N1—C4—H4B109.1
C5—C6—H6A109.4C3—C4—H4B109.1
C2—C6—H6A109.4H4A—C4—H4B107.9
C5—C6—H6B109.4
C5—N1—C7—C8−61.51 (17)C2—C6—C5—N157.80 (18)
C4—N1—C7—C8178.78 (14)C11—C12—C13—C8−0.5 (3)
C6—C2—C1—O1−70.76 (18)C9—C8—C13—C12−0.7 (3)
C3—C2—C1—O1166.27 (13)C7—C8—C13—C12179.08 (16)
C10—C9—C8—C130.9 (3)C1—C2—C3—C4−179.95 (16)
C10—C9—C8—C7−178.82 (16)C6—C2—C3—C455.06 (18)
N1—C7—C8—C13−75.6 (2)C9—C10—C11—O2179.45 (15)
N1—C7—C8—C9104.14 (19)C9—C10—C11—C12−1.1 (2)
C1—C2—C6—C5179.30 (15)C13—C12—C11—O2−179.23 (16)
C3—C2—C6—C5−55.54 (18)C13—C12—C11—C101.4 (2)
C8—C9—C10—C110.0 (3)C5—N1—C4—C357.90 (18)
C4—N1—C5—C6−57.51 (17)C7—N1—C4—C3177.44 (15)
C7—N1—C5—C6−176.24 (14)C2—C3—C4—N1−57.70 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N1i0.78 (3)2.04 (3)2.813 (2)174 (3)
O2—H2···O1ii0.89 (2)1.82 (2)2.702 (2)176 (2)
Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) x, y, z+1.

Experimental details

Crystal data
Chemical formulaC13H19NO2
Mr221.29
Crystal system, space groupMonoclinic, Cc
Temperature (K)150
a, b, c (Å)6.0428 (2), 17.2269 (7), 11.3010 (4)
β (°) 94.663 (4)
V (Å3)1172.53 (7)
Z4
Radiation typeMo Kα
µ (mm−1)0.08
Crystal size (mm)0.64 × 0.15 × 0.07
Data collection
DiffractometerOxford Diffraction Xcalibur Atlas Gemini Ultra CCD
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		5289, 1474, 1326
Rint0.021
(sin θ/λ)max (Å−1)0.692
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.084, 1.08
No. of reflections1474
No. of parameters151
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.23, −0.16

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N1i0.78 (3)2.04 (3)2.813 (2)174 (3)
O2—H2···O1ii0.89 (2)1.82 (2)2.702 (2)176 (2)
Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) x, y, z+1.
 

Acknowledgements

This work was supported by Brazilian agencies FAPEMIG (APQ-01072–08, APQ-02685–09 and APQ-01093–10), FINEP (refs. 0134/08 and 0336/09), CNPq (306867/2009–5 and 476870/2011–9) and CAPES (PNPD-2007, PNPD-2011). We are also grateful to the Brazilian agencies for providing fellowships to IMRL (CAPES), MCRS (CAPES), MM (FAPEMIG). Thanks are due to the Consejo Superior de Investigaciones Científicas (CSIC) of Spain for the award of a license for the use of the Cambridge Structural Database (CSD). The authors express sincere thanks to LabCri-UFMG for measurements and support of the X-ray facilities.

References

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ISSN: 2056-9890
Volume 68| Part 7| July 2012| Pages o2275-o2276
https://doi.org/10.1107/S1600536812028838
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