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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 6| June 2012| Pages o1603-o1604
doi:10.1107/S1600536812019022

N-Hexyl-3-(4-hy­dr­oxy-3,5-dimeth­­oxy­phen­yl)propanamide

L. C. R. Andrade,a J. A. Paixão,a* M. J. M. de Almeida,a E. J. Tavares da Silvab and F. M. Fernandes Roleirab

aCEMDRX, Department of Physics, Faculty of Sciences and Technology, University of Coimbra, P-3004-516 Coimbra, Portugal, and bCenter for Pharmaceutical Studies, Pharmaceutical Chemistry Group, Faculty of Pharmacy, University of Coimbra, P-3000-548 Coimbra, Portugal
*Correspondence e-mail: jap@pollux.fis.uc.pt

(Received 20 April 2012; accepted 27 April 2012; online 2 May 2012)

In the title compound, C17H27NO4, which is an hydro­sinapic acid derivative with increased lipophilicity conferred by an additional alkyl chain, the central and the hexyl linear chains contain slightly shorter bond lengths [C—N = 1.316 (2) Å; average linear chain C—C = 1.487 (6) Å] than reported average values [Csp2—N = 1.334, C—C for CH2—CH2 = 1.524 and 1.513 Å for CH2—CH3]. The 4-hy­droxy-3,5-dimeth­oxy­phenyl plane [r.m.s. deviation 0.055 (12) Å] makes an angle of 59.89 (5)° with the central plane of the mol­ecule (composed of the N atom, the carbonyl group and the two methyl­ene C atoms linking the carbonyl group and the ring, [r.m.s. deviation 0.0026 (10) Å], which, in turn, makes an angle of 64.24 (13)° with the essentially planar hexyl chain [r.m.s. deviation 0.035 (18) Å]. The N—H group of the amide group is involved in a bifurcated hydrogen bond towards the hy­droxy and one of the meth­oxy O atoms of the 4-hy­droxy-3,5-dimeth­oxy­phenyl substituent of a neighbouring mol­ecule, forming a two-dimensional network in the (100) plane. In addition, the same hy­droxy group acts as a donor towards the carbonyl O atom of another neighbouring mol­ecule, forming chains running along the b axis.

Related literature

For the dependence on their structural characteristics of the anti­cancer activity of phenolic acids and their derivatives, see: Gomes et al. (2003[Gomes, C. A., da Cruz, T. G., Andrade, J. L., Milhazes, N., Borges, F. & Marques, M. P. (2003). J. Med. Chem. 46, 5395-5401.]). For restrictions on protection of lipophilic systems due to the hydro­philic nature of mol­ecules in aqueous media, see: Gao & Hu (2010[Gao, S. & Hu, M. (2010). Mini Rev. Med. Chem. 10, 550-567.]). For the synthesis, see: Roleira et al. (2010[Roleira, F. M. F., Siquet, C., Elisabeta Orru, E., Garrido, E. M., Garrido, J., Milhazes, N., Podda, G., Paiva-Martins, F., Reis, S., Carvalho, R. A., Tavares-da-Silva, E. J. & Borges, F. (2010). Bioorg. Med. Chem. 18, 5816-5825.]). For reference 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

  • C17H27NO4

  • Mr = 309.40

  • Monoclinic, P 21 /c

  • a = 19.1126 (5) Å

  • b = 8.4086 (2) Å

  • c = 11.0715 (3) Å

  • β = 91.5691 (15)°

  • V = 1778.64 (8) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 293 K

  • 0.34 × 0.26 × 0.19 mm
Data collection

  • Bruker APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2000[Sheldrick, G. M. (2000). SADABS. University of Göttingen, Germany.]) Tmin = 0.856, Tmax = 0.865

  • 34604 measured reflections

  • 4259 independent reflections

  • 2478 reflections with I > 2σ(I)

  • Rint = 0.038
Refinement

  • R[F2 > 2σ(F2)] = 0.048

  • wR(F2) = 0.172

  • S = 0.99

  • 4255 reflections

  • 204 parameters

  • H-atom parameters constrained

  • Δρmax = 0.19 e Å−3

  • Δρmin = −0.15 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N—H10⋯O4i 0.86 2.16 2.9655 (19) 155
N—H10⋯O5i 0.86 2.55 3.244 (2) 138
O4—H4⋯O9ii 0.82 1.84 2.6216 (17) 158
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) x, y+1, z.

Data collection: SMART (Bruker, 2006[Bruker (2006). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: PLATON (Spek, 2009)[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]; software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812019022/bt5889sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812019022/bt5889Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812019022/bt5889Isup3.cml

checkCIF report


Comment top

Hydroxycinnamic acids and derivatives are known to display relevant antioxidant properties as well as biological activity towards several tumor cells, with their growth-inhibitory potency being strongly dependent on their structural characteristics (Gomes et al., 2003). Despite all the interesting biological effects of hydroxycinnamic acids and despite being dietary components, their bioavailability presents some limitations: although working well in aqueous media, their hydrophilic nature is usually a restriction for lipophilic systems protection (Gao & Hu, 2010). In order to develop new and more effective phenolic agents suitable for chemopreventive and/or chemotherapeutic purposes, hydrosinapic acid derivatives with increased lipophilicity conferred by an additional alkyl chain, were developed. For this, N-hexyl-3-(4-hydroxy-3,5-dimethoxyphenyl)propanamide was synthesized by reaction of the corresponding acid with hexylamine, in the presence of the coupling agent (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP) (Roleira et al., 2010). Single crystal X-ray measurements evidence normal bond length values for the phenyl ring and its substituents. However the Csp2–N bond length in the molecule's central chain [1.316 (2) Å] is shorter than the reported average value of 1.334 Å (Allen et al., 1987). Furthermore the average value of the five measured Csp3–Csp3 bond lengths of the hexyl chain [1.487 (6) Å] is also significantly shorter then the average reported values (1.524 for CH2–CH2 and 1.513 for CH2–CH3, Allen et al., 1987). The molecule is characterized by an intramolecular C11–H11A···O9 pseudo-hydrogen bond within the central chain plane (deviation 0.0026 Å). The dihedral angle between this plane and the phenyl one (deviation 0.0545 Å) is 59.89 (5)°, being 64.24 (13)° the corresponding value between the central plane and the one of the hexyl chain (deviation 0.0349 Å). Cohesion of the structure is obtained through an extended newtork of H-bonds. The H atom of the amide group is involved in a bifurcated H-bond towards the hydroxy and one of the methoxy O atoms of the 4-hydroxy-3,5-dimethoxyphenyl substituent of a neignhbour molecule, forming a two dimensional network in the (100) plane. In addition, the same hydroxy group acts as a donnor towards the carbonyl O atom of another neighbour molecule forming chains running along the b axis.

Related literature top

For the dependence on their structural characteristics of the anticancer activity of phenolic acids and their derivatives, see: Gomes et al. (2003). For restrictions on protection of lipophilic systems due to the hydrophilic nature of molecules in aqueous media, see: Gao & Hu (2010). For the synthesis, see: Roleira et al. (2010). For reference bond lengths, see: Allen et al. (1987).

Experimental top

The title amide was prepared from the 3-(4-hydroxy-3,5-dimethoxyphenyl)propanoic acid by dissolution of 5 mmol of the acid in 10 ml of DMF followed by the addition of triethylamine (0.7 ml, 5 mmol). The solution was cooled in an ice-water bath and 0.657 ml (5 mmol) of N-hexylamine were added followed by a solution of 2.21 g (5 mmol) of BOP in 10 ml of methylene chloride. The mixture was stirred at 273 K for 30 min and then at room temperature for 30 min. Methylene chloride was removed under reduced pressure and the solution was diluted with 150 ml of water and extracted with ethyl acetate (150 ml). The organic phase was washed successively with 1 N hydrochloride acid (3x100 ml), water (150 ml), 1M NaHCO3 (3x100 ml), and water (2x100 ml), dried over anhydrous magnesium sulfate, filtered and evaporated, affording a crude material which was purified by crystallization yielding the desired amide. Suitable crystals for X-ray analysis were grown from slow evaporation of ethyl acetate. Mp(ethyl acetate): 366–367 K; IR (ATR) υmax cm-1: 3319 (N—H stretch), 1643 (C═O), 1125 (C–O).

Refinement top

All hydrogen atoms were placed at idealized positions and refined as riding on their parent atoms using SHELXL97 defaults; the hydroxyl H atom was initialy positioned at the maximum of the difference electronic density around the parent O atom and refined using the HFIX 147 instruction.

Only 4255 out of 4259 independent reflections were used in the refinement because 4 low angle reflections were omitted due to overshadowing from the beam-stop.

Computing details top

Data collection: SMART (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. ORTEPII plot of the title compound. Displacement ellipsoids are drawn at the 50% level.
[Figure 2] Fig. 2. Diagram depicting the H-bond network.
N-Hexyl-3-(4-hydroxy-3,5-dimethoxyphenyl)propanamide top
Crystal data top
C17H27NO4Dx = 1.157 Mg m−3
Mr = 309.40Melting point: 366.5 K
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 19.1126 (5) ÅCell parameters from 7386 reflections
b = 8.4086 (2) Åθ = 3.0–23.3°
c = 11.0715 (3) ŵ = 0.08 mm−1
β = 91.5691 (15)°T = 293 K
V = 1778.64 (8) Å3Prism, colourless
Z = 40.34 × 0.26 × 0.19 mm
F(000) = 672
Data collection top
Bruker APEX CCD
diffractometer		4259 independent reflections
Radiation source: fine-focus sealed tube2478 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
ϕ and ω scansθmax = 27.9°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2000)		h = −25→25
Tmin = 0.856, Tmax = 0.865k = −11→9
34604 measured reflectionsl = −12→14
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)] = 0.048H-atom parameters constrained
wR(F2) = 0.172 w = 1/[σ2(Fo2) + (0.094P)2 + 0.1703P]
where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max < 0.001
4255 reflectionsΔρmax = 0.19 e Å−3
204 parametersΔρmin = −0.15 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: 0.014 (3)
Crystal data top
C17H27NO4V = 1778.64 (8) Å3
Mr = 309.40Z = 4
Monoclinic, P21/cMo Kα radiation
a = 19.1126 (5) ŵ = 0.08 mm−1
b = 8.4086 (2) ÅT = 293 K
c = 11.0715 (3) Å0.34 × 0.26 × 0.19 mm
β = 91.5691 (15)°
Data collection top
Bruker APEX CCD
diffractometer		4259 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2000)		2478 reflections with I > 2σ(I)
Tmin = 0.856, Tmax = 0.865Rint = 0.038
34604 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.172H-atom parameters constrained
S = 0.99Δρmax = 0.19 e Å−3
4255 reflectionsΔρmin = −0.15 e Å−3
204 parameters
Special details top

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
N0.75497 (7)−0.11966 (19)0.21012 (13)0.0636 (4)
H100.7363−0.05640.26100.076*
O30.58084 (7)0.45097 (14)0.08943 (12)0.0698 (4)
O40.67504 (7)0.49686 (13)−0.08385 (10)0.0651 (4)
H40.68770.5478−0.02400.098*
O50.73329 (7)0.25857 (15)−0.19467 (11)0.0676 (4)
O90.73578 (7)−0.30205 (15)0.06653 (12)0.0689 (4)
C10.61840 (9)0.03560 (18)0.00631 (14)0.0507 (4)
C20.58855 (9)0.16335 (19)0.06493 (15)0.0523 (4)
H20.55550.14540.12360.063*
C30.60757 (9)0.31751 (18)0.03669 (15)0.0511 (4)
C40.65672 (9)0.34669 (18)−0.05009 (14)0.0485 (4)
C50.68601 (9)0.21800 (19)−0.10955 (14)0.0510 (4)
C60.66706 (9)0.06345 (19)−0.08136 (14)0.0528 (4)
H60.6871−0.0216−0.12150.063*
C70.59855 (9)−0.13192 (19)0.04171 (16)0.0585 (5)
H7A0.6098−0.2039−0.02340.070*
H7B0.5484−0.13680.05250.070*
C80.63594 (9)−0.18697 (19)0.15739 (15)0.0549 (4)
H8A0.6284−0.10970.22080.066*
H8B0.6161−0.28740.18260.066*
C90.71300 (9)−0.20718 (18)0.14130 (15)0.0501 (4)
C110.83047 (10)−0.1231 (3)0.20557 (19)0.0850 (7)
H11A0.8472−0.01630.19000.102*
H11B0.8438−0.18970.13850.102*
C120.86543 (12)−0.1833 (3)0.3176 (2)0.0894 (7)
H12A0.8501−0.29160.33160.107*
H12B0.8508−0.11920.38520.107*
C130.94383 (12)−0.1808 (4)0.3140 (2)0.0967 (8)
H13A0.9580−0.24790.24770.116*
H13B0.9585−0.07310.29590.116*
C140.98230 (14)−0.2337 (4)0.4256 (3)0.1093 (9)
H14A0.9668−0.16950.49270.131*
H14B0.9694−0.34300.44200.131*
C151.05973 (14)−0.2242 (4)0.4222 (3)0.1218 (11)
H15A1.0751−0.28760.35470.146*
H15B1.0726−0.11480.40640.146*
C161.09856 (17)−0.2777 (5)0.5325 (3)0.1430 (13)
H16A1.0904−0.38910.54480.215*
H16B1.0828−0.21910.60090.215*
H16C1.1477−0.25970.52320.215*
C330.52544 (11)0.4316 (2)0.1699 (2)0.0792 (6)
H33A0.54150.37070.23860.119*
H33B0.48740.37670.12960.119*
H33C0.50980.53400.19620.119*
C550.76020 (12)0.1358 (3)−0.26704 (19)0.0827 (6)
H55A0.72220.0765−0.30330.124*
H55B0.78880.0663−0.21780.124*
H55C0.78790.1812−0.32930.124*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N0.0518 (10)0.0748 (10)0.0642 (9)−0.0007 (7)0.0016 (7)−0.0170 (8)
O30.0784 (9)0.0481 (7)0.0842 (9)0.0003 (6)0.0272 (7)−0.0118 (6)
O40.0938 (10)0.0483 (7)0.0537 (7)−0.0083 (6)0.0098 (6)0.0001 (5)
O50.0770 (9)0.0656 (8)0.0611 (7)−0.0018 (6)0.0200 (6)−0.0086 (6)
O90.0729 (9)0.0600 (8)0.0742 (8)−0.0011 (6)0.0102 (7)−0.0160 (6)
C10.0504 (10)0.0457 (8)0.0552 (9)−0.0015 (7)−0.0134 (7)−0.0021 (7)
C20.0495 (10)0.0502 (9)0.0573 (9)−0.0036 (7)0.0020 (8)−0.0012 (8)
C30.0548 (10)0.0442 (9)0.0542 (9)0.0016 (7)0.0003 (7)−0.0063 (7)
C40.0572 (10)0.0426 (8)0.0456 (8)−0.0020 (7)−0.0018 (7)−0.0009 (7)
C50.0501 (10)0.0564 (9)0.0465 (8)0.0004 (7)−0.0017 (7)−0.0027 (7)
C60.0567 (11)0.0459 (9)0.0555 (9)0.0053 (7)−0.0059 (8)−0.0087 (7)
C70.0545 (11)0.0464 (9)0.0740 (11)−0.0066 (7)−0.0105 (8)−0.0046 (8)
C80.0560 (11)0.0468 (9)0.0619 (10)−0.0064 (7)0.0044 (8)0.0031 (8)
C90.0576 (11)0.0419 (8)0.0508 (9)0.0010 (7)0.0026 (7)0.0053 (7)
C110.0564 (13)0.1206 (19)0.0779 (13)−0.0055 (12)0.0030 (10)−0.0124 (13)
C120.0622 (14)0.1089 (18)0.0967 (16)−0.0005 (12)−0.0056 (12)0.0081 (14)
C130.0641 (15)0.133 (2)0.0928 (16)0.0082 (13)−0.0021 (12)−0.0075 (15)
C140.0774 (18)0.138 (2)0.112 (2)0.0045 (16)−0.0112 (15)0.0073 (18)
C150.0728 (18)0.184 (3)0.108 (2)0.0236 (18)−0.0101 (15)−0.012 (2)
C160.104 (2)0.209 (4)0.115 (2)0.016 (2)−0.0206 (19)0.005 (2)
C330.0720 (14)0.0728 (13)0.0943 (14)−0.0026 (10)0.0296 (11)−0.0245 (12)
C550.0834 (16)0.0945 (16)0.0711 (12)0.0065 (12)0.0193 (11)−0.0207 (12)
Geometric parameters (Å, º) top
N—C91.316 (2)C11—C121.482 (3)
N—C111.446 (2)C11—H11A0.9700
N—H100.8600C11—H11B0.9700
O3—C31.3703 (19)C12—C131.500 (3)
O3—C331.412 (2)C12—H12A0.9700
O4—C41.3653 (19)C12—H12B0.9700
O4—H40.8200C13—C141.489 (3)
O5—C51.367 (2)C13—H13A0.9700
O5—C551.412 (2)C13—H13B0.9700
O9—C91.2373 (19)C14—C151.484 (3)
C1—C61.383 (2)C14—H14A0.9700
C1—C21.386 (2)C14—H14B0.9700
C1—C71.513 (2)C15—C161.481 (4)
C2—C31.384 (2)C15—H15A0.9700
C2—H20.9300C15—H15B0.9700
C3—C41.384 (2)C16—H16A0.9600
C4—C51.392 (2)C16—H16B0.9600
C5—C61.387 (2)C16—H16C0.9600
C6—H60.9300C33—H33A0.9600
C7—C81.522 (2)C33—H33B0.9600
C7—H7A0.9700C33—H33C0.9600
C7—H7B0.9700C55—H55A0.9600
C8—C91.498 (2)C55—H55B0.9600
C8—H8A0.9700C55—H55C0.9600
C8—H8B0.9700
C9—N—C11124.19 (16)H11A—C11—H11B107.7
C9—N—H10117.9C11—C12—C13113.6 (2)
C11—N—H10117.9C11—C12—H12A108.8
C3—O3—C33117.97 (14)C13—C12—H12A108.8
C4—O4—H4109.5C11—C12—H12B108.8
C5—O5—C55117.83 (15)C13—C12—H12B108.8
C6—C1—C2119.40 (15)H12A—C12—H12B107.7
C6—C1—C7121.18 (15)C14—C13—C12116.4 (2)
C2—C1—C7119.40 (16)C14—C13—H13A108.2
C3—C2—C1120.40 (16)C12—C13—H13A108.2
C3—C2—H2119.8C14—C13—H13B108.2
C1—C2—H2119.8C12—C13—H13B108.2
O3—C3—C4114.75 (14)H13A—C13—H13B107.3
O3—C3—C2124.57 (16)C15—C14—C13115.7 (2)
C4—C3—C2120.68 (15)C15—C14—H14A108.4
O4—C4—C3122.55 (14)C13—C14—H14A108.4
O4—C4—C5118.68 (15)C15—C14—H14B108.4
C3—C4—C5118.68 (14)C13—C14—H14B108.4
O5—C5—C6124.80 (15)H14A—C14—H14B107.4
O5—C5—C4114.47 (14)C16—C15—C14116.1 (3)
C6—C5—C4120.73 (16)C16—C15—H15A108.3
C1—C6—C5120.10 (15)C14—C15—H15A108.3
C1—C6—H6119.9C16—C15—H15B108.3
C5—C6—H6119.9C14—C15—H15B108.3
C1—C7—C8112.70 (13)H15A—C15—H15B107.4
C1—C7—H7A109.1C15—C16—H16A109.5
C8—C7—H7A109.1C15—C16—H16B109.5
C1—C7—H7B109.1H16A—C16—H16B109.5
C8—C7—H7B109.1C15—C16—H16C109.5
H7A—C7—H7B107.8H16A—C16—H16C109.5
C9—C8—C7112.03 (14)H16B—C16—H16C109.5
C9—C8—H8A109.2O3—C33—H33A109.5
C7—C8—H8A109.2O3—C33—H33B109.5
C9—C8—H8B109.2H33A—C33—H33B109.5
C7—C8—H8B109.2O3—C33—H33C109.5
H8A—C8—H8B107.9H33A—C33—H33C109.5
O9—C9—N121.86 (16)H33B—C33—H33C109.5
O9—C9—C8121.18 (15)O5—C55—H55A109.5
N—C9—C8116.96 (15)O5—C55—H55B109.5
N—C11—C12113.90 (19)H55A—C55—H55B109.5
N—C11—H11A108.8O5—C55—H55C109.5
C12—C11—H11A108.8H55A—C55—H55C109.5
N—C11—H11B108.8H55B—C55—H55C109.5
C12—C11—H11B108.8
C6—C1—C2—C3−0.4 (2)C2—C1—C6—C50.4 (2)
C7—C1—C2—C3177.97 (15)C7—C1—C6—C5−177.97 (14)
C33—O3—C3—C4173.79 (16)O5—C5—C6—C1−179.81 (14)
C33—O3—C3—C2−6.2 (3)C4—C5—C6—C10.2 (2)
C1—C2—C3—O3179.82 (15)C6—C1—C7—C899.72 (18)
C1—C2—C3—C4−0.2 (2)C2—C1—C7—C8−78.67 (19)
O3—C3—C4—O4−2.5 (2)C1—C7—C8—C9−67.73 (19)
C2—C3—C4—O4177.49 (14)C11—N—C9—O90.6 (3)
O3—C3—C4—C5−179.18 (14)C11—N—C9—C8−179.38 (17)
C2—C3—C4—C50.8 (2)C7—C8—C9—O9−60.08 (19)
C55—O5—C5—C66.1 (2)C7—C8—C9—N119.90 (16)
C55—O5—C5—C4−173.98 (16)C9—N—C11—C12−115.0 (2)
O4—C4—C5—O52.4 (2)N—C11—C12—C13−177.8 (2)
C3—C4—C5—O5179.19 (14)C11—C12—C13—C14177.6 (2)
O4—C4—C5—C6−177.66 (15)C12—C13—C14—C15−177.6 (3)
C3—C4—C5—C6−0.8 (2)C13—C14—C15—C16−179.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N—H10···O4i0.862.162.9655 (19)155
N—H10···O5i0.862.553.244 (2)138
O4—H4···O9ii0.821.842.6216 (17)158
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC17H27NO4
Mr309.40
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)19.1126 (5), 8.4086 (2), 11.0715 (3)
β (°) 91.5691 (15)
V (Å3)1778.64 (8)
Z4
Radiation typeMo Kα
µ (mm−1)0.08
Crystal size (mm)0.34 × 0.26 × 0.19
Data collection
DiffractometerBruker APEX CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2000)
Tmin, Tmax0.856, 0.865
No. of measured, independent and
observed [I > 2σ(I)] reflections		34604, 4259, 2478
Rint0.038
(sin θ/λ)max (Å−1)0.659
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.172, 0.99
No. of reflections4255
No. of parameters204
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.19, −0.15

Computer programs: SMART (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N—H10···O4i0.862.162.9655 (19)155.1
N—H10···O5i0.862.553.244 (2)138.1
O4—H4···O9ii0.821.842.6216 (17)158.3
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, y+1, z.
 

Acknowledgements

This work was supported by funds from FEDER via the COMPETE (Programa Operacional Factores de Competi­tivi­dade) programme and by the FCT (Fundação para a Ciência e a Tecnologia; project PEst-C/FIS/UI0036/2011).

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
 First citationBruker (2006). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationGao, S. & Hu, M. (2010). Mini Rev. Med. Chem. 10, 550–567.  CrossRef CAS PubMed Google Scholar
 First citationGomes, C. A., da Cruz, T. G., Andrade, J. L., Milhazes, N., Borges, F. & Marques, M. P. (2003). J. Med. Chem. 46, 5395–5401.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationRoleira, F. M. F., Siquet, C., Elisabeta Orru, E., Garrido, E. M., Garrido, J., Milhazes, N., Podda, G., Paiva-Martins, F., Reis, S., Carvalho, R. A., Tavares-da-Silva, E. J. & Borges, F. (2010). Bioorg. Med. Chem. 18, 5816–5825.  Web of Science CrossRef CAS PubMed Google Scholar
 First citationSheldrick, G. M. (2000). SADABS. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890
Volume 68| Part 6| June 2012| Pages o1603-o1604
doi:10.1107/S1600536812019022
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