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

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ISSN: 2056-9890

2-(4-Iso­butyl­phen­yl)-1-(morpholin-4-yl)propan-1-one

aInstitute of Chemical Sciences, University of Peshawar, Peshawar, Pakistan, and bUniversity of Sargodha, Department of Physics, Sargodha, Pakistan
*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 23 July 2012; accepted 24 July 2012; online 4 August 2012)

In the title compound, C17H25NO2, the morpholine ring adopts a chair conformation. The benzene ring makes a dihedral angle of 39.81 (13)° with the basal plane of the morpholine group.

Related literature

For related structures, see: Hansen et al. (2003[Hansen, L. K., Perlovich, G. L. & Bauer-Brandl, A. (2003). Acta Cryst. E59, o1357-o1358.]); Nasirullah et al. (2012[Nasirullah, Islam, N. U., Tahir, M. N., Khan, I. & Zulfiqar, M. (2012). Acta Cryst. E68, o2636.]).

[Scheme 1]

Experimental

Crystal data
  • C17H25NO2

  • Mr = 275.38

  • Monoclinic, P 21 /c

  • a = 14.1389 (19) Å

  • b = 10.3358 (15) Å

  • c = 11.3552 (15) Å

  • β = 103.426 (8)°

  • V = 1614.1 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.07 mm−1

  • T = 296 K

  • 0.32 × 0.14 × 0.12 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.977, Tmax = 0.990

  • 11200 measured reflections

  • 2835 independent reflections

  • 1246 reflections with I > 2σ(I)

  • Rint = 0.100

Refinement
  • R[F2 > 2σ(F2)] = 0.062

  • wR(F2) = 0.159

  • S = 0.98

  • 2835 reflections

  • 185 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.17 e Å−3

  • Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 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: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

The title compound, (Fig. 1) has been synthesized for the purpose of biological studies. The crystal structure of S(+)-2-(4-isobutylphenyl)propionic acid (Hansen et al., 2003) has been published; this is related to the present structure by replacement of the carboxyl OH group by the morpholine ring. Also, we have recently submitted to this journal the crystal structure of 2-(6-methoxynaphthalen-2-yl)-1-morpholinopropan-1-one (Nasirullah et al., 2012).

In the title compound, the benzene ring A (C5–C10) and the basal plane B (C14–C17) of the morpholine ring make a dihedral angle of 39.81 (13)°. The morpholine ring adopts a chair conformation, in which atoms N1 and O2 are at distances of -0.623 (5) Å and 0.652 (5) Å, respectively, from the basal plane B.

The crystal structure does not exhibit hydrogen bonding.

Related literature top

For related structures, see: Hansen et al. (2003); Nasirullah et al. (2012).

Experimental top

A mixture of morpholine (0.54 g, 6.2 mmol) and ibuprofen acid chloride (0.7 g, 3.1 mmol) in 15 ml of dichloromethane was stirred at room temperature for 3 h. After completion of the reaction, the reaction mixture was filtered and the solvent was evaporated, resulting in a crude product which was purified by flash chromatography. Evaporation of solvent yielded the title compound as white crystalline needles. Yield: 84.0%.

Refinement top

The H atoms were positioned geometrically and refined as riding: Csp2—H = 0.93 Å, Cmethyl—H = 0.96 Å, Cmethylene—H = 0.97 Å and Cmethine—H = 0.98 Å. Uiso(H) = xUeq(C), where x = 1.5 for methyl H and x = 1.2 for all other H atoms.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. View of the title compound with displacement ellipsoids drawn at the 50% probability level. Hydrogen atoms are shown as spheres of arbitrary radius.
2-(4-Isobutylphenyl)-1-(morpholin-4-yl)propan-1-one top
Crystal data top
C17H25NO2F(000) = 600
Mr = 275.38Dx = 1.133 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1246 reflections
a = 14.1389 (19) Åθ = 1.5–25.0°
b = 10.3358 (15) ŵ = 0.07 mm1
c = 11.3552 (15) ÅT = 296 K
β = 103.426 (8)°Needle, white
V = 1614.1 (4) Å30.32 × 0.14 × 0.12 mm
Z = 4
Data collection top
Bruker Kappa APEXII CCD
diffractometer
2835 independent reflections
Radiation source: fine-focus sealed tube1246 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.100
Detector resolution: 8.20 pixels mm-1θmax = 25.0°, θmin = 1.5°
ω scansh = 1616
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 1212
Tmin = 0.977, Tmax = 0.990l = 1313
11200 measured reflections
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)] = 0.062H-atom parameters constrained
wR(F2) = 0.159 w = 1/[σ2(Fo2) + (0.0542P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.98(Δ/σ)max < 0.001
2835 reflectionsΔρmax = 0.17 e Å3
185 parametersΔρmin = 0.16 e Å3
1 restraintExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0053 (13)
Crystal data top
C17H25NO2V = 1614.1 (4) Å3
Mr = 275.38Z = 4
Monoclinic, P21/cMo Kα radiation
a = 14.1389 (19) ŵ = 0.07 mm1
b = 10.3358 (15) ÅT = 296 K
c = 11.3552 (15) Å0.32 × 0.14 × 0.12 mm
β = 103.426 (8)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer
2835 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
1246 reflections with I > 2σ(I)
Tmin = 0.977, Tmax = 0.990Rint = 0.100
11200 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0621 restraint
wR(F2) = 0.159H-atom parameters constrained
S = 0.98Δρmax = 0.17 e Å3
2835 reflectionsΔρmin = 0.16 e Å3
185 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
O10.35601 (17)0.2845 (2)0.5282 (2)0.0581 (10)
O20.61970 (19)0.4915 (2)0.7983 (2)0.0731 (12)
N10.4656 (2)0.3220 (2)0.7033 (2)0.0433 (10)
C10.0388 (3)0.9627 (4)0.8327 (4)0.097 (2)
C20.0646 (3)0.8359 (3)0.7788 (3)0.0655 (17)
C30.0182 (3)0.8282 (4)0.6453 (4)0.098 (2)
C40.1743 (3)0.8188 (3)0.8061 (3)0.0567 (17)
C50.2088 (2)0.6854 (3)0.7822 (3)0.0437 (12)
C60.2300 (3)0.6539 (3)0.6736 (3)0.0567 (16)
C70.2579 (3)0.5313 (3)0.6491 (3)0.0540 (14)
C80.2674 (2)0.4342 (3)0.7350 (3)0.0374 (12)
C90.2484 (2)0.4655 (3)0.8451 (3)0.0464 (12)
C100.2196 (3)0.5887 (3)0.8674 (3)0.0497 (14)
C110.2928 (2)0.2963 (3)0.7066 (3)0.0406 (12)
C120.2036 (3)0.2257 (4)0.6335 (3)0.0656 (17)
C130.3738 (3)0.2981 (3)0.6387 (3)0.0429 (14)
C140.5436 (3)0.3446 (3)0.6411 (3)0.0536 (14)
C150.5844 (3)0.4767 (3)0.6721 (3)0.0636 (17)
C160.5431 (3)0.4735 (4)0.8584 (3)0.0660 (16)
C170.4977 (3)0.3419 (3)0.8333 (3)0.0467 (12)
H1A0.030540.972550.814800.1454*
H1B0.067081.033650.798430.1454*
H1C0.063820.961560.918890.1454*
H20.037960.765130.818720.0784*
H3A0.035620.747810.613550.1464*
H3B0.040780.898860.604160.1464*
H3C0.051170.833090.633030.1464*
H4A0.200660.880500.757830.0682*
H4B0.200750.839860.890560.0682*
H60.225320.717650.614710.0681*
H70.270590.513410.573970.0647*
H90.255070.402780.905150.0556*
H100.207030.606940.942480.0595*
H110.316280.250100.783160.0487*
H12A0.220520.137880.619920.0984*
H12B0.180770.268340.557040.0984*
H12C0.153190.226330.677450.0984*
H14A0.518440.337360.554280.0646*
H14B0.594220.280190.665860.0646*
H15A0.636990.491560.631910.0764*
H15B0.534330.540680.642760.0764*
H16A0.493830.539240.831790.0792*
H16B0.568300.483640.944960.0792*
H17A0.544650.275920.868160.0561*
H17B0.442610.334790.870380.0561*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0606 (18)0.0754 (18)0.0365 (15)0.0023 (14)0.0078 (12)0.0122 (12)
O20.069 (2)0.079 (2)0.076 (2)0.0311 (16)0.0263 (16)0.0203 (15)
N10.0424 (19)0.0540 (19)0.0348 (16)0.0021 (15)0.0119 (15)0.0046 (13)
C10.082 (4)0.076 (3)0.130 (4)0.031 (3)0.018 (3)0.027 (3)
C20.053 (3)0.057 (3)0.084 (3)0.011 (2)0.011 (2)0.005 (2)
C30.077 (4)0.111 (4)0.090 (3)0.027 (3)0.011 (3)0.020 (3)
C40.056 (3)0.054 (3)0.059 (3)0.001 (2)0.011 (2)0.0066 (18)
C50.041 (2)0.046 (2)0.046 (2)0.0025 (18)0.0137 (18)0.0063 (19)
C60.072 (3)0.044 (2)0.058 (3)0.015 (2)0.023 (2)0.0139 (18)
C70.074 (3)0.054 (2)0.038 (2)0.011 (2)0.0209 (19)0.0030 (19)
C80.036 (2)0.042 (2)0.035 (2)0.0020 (16)0.0101 (15)0.0018 (16)
C90.052 (2)0.048 (2)0.040 (2)0.0067 (19)0.0123 (18)0.0058 (17)
C100.059 (3)0.055 (2)0.037 (2)0.003 (2)0.0149 (18)0.0054 (19)
C110.039 (2)0.041 (2)0.042 (2)0.0008 (17)0.0099 (17)0.0021 (16)
C120.049 (3)0.068 (3)0.078 (3)0.010 (2)0.011 (2)0.018 (2)
C130.049 (3)0.040 (2)0.040 (2)0.0022 (18)0.0108 (19)0.0050 (16)
C140.047 (2)0.068 (3)0.051 (2)0.003 (2)0.022 (2)0.0057 (19)
C150.067 (3)0.065 (3)0.066 (3)0.007 (2)0.030 (2)0.006 (2)
C160.071 (3)0.074 (3)0.057 (2)0.020 (2)0.023 (2)0.019 (2)
C170.048 (2)0.054 (2)0.038 (2)0.0046 (18)0.0096 (17)0.0034 (16)
Geometric parameters (Å, º) top
O1—C131.229 (4)C1—H1C0.9600
O2—C151.412 (4)C2—H20.9800
O2—C161.420 (5)C3—H3A0.9600
N1—C131.357 (5)C3—H3B0.9600
N1—C141.460 (5)C3—H3C0.9600
N1—C171.455 (4)C4—H4A0.9700
C1—C21.526 (5)C4—H4B0.9700
C2—C31.508 (6)C6—H60.9300
C2—C41.520 (6)C7—H70.9300
C4—C51.508 (5)C9—H90.9300
C5—C61.374 (5)C10—H100.9300
C5—C101.375 (5)C11—H110.9800
C6—C71.375 (5)C12—H12A0.9600
C7—C81.384 (5)C12—H12B0.9600
C8—C91.377 (5)C12—H12C0.9600
C8—C111.523 (4)C14—H14A0.9700
C9—C101.378 (5)C14—H14B0.9700
C11—C121.525 (5)C15—H15A0.9700
C11—C131.522 (5)C15—H15B0.9700
C14—C151.492 (5)C16—H16A0.9700
C16—C171.503 (5)C16—H16B0.9700
C1—H1A0.9600C17—H17A0.9700
C1—H1B0.9600C17—H17B0.9700
C15—O2—C16110.1 (3)C2—C4—H4A108.00
C13—N1—C14120.2 (3)C2—C4—H4B108.00
C13—N1—C17127.5 (3)C5—C4—H4A108.00
C14—N1—C17112.1 (3)C5—C4—H4B108.00
C1—C2—C3111.1 (3)H4A—C4—H4B108.00
C1—C2—C4110.2 (3)C5—C6—H6119.00
C3—C2—C4112.6 (3)C7—C6—H6119.00
C2—C4—C5115.3 (3)C6—C7—H7120.00
C4—C5—C6121.7 (3)C8—C7—H7120.00
C4—C5—C10121.7 (3)C8—C9—H9120.00
C6—C5—C10116.6 (3)C10—C9—H9120.00
C5—C6—C7122.2 (3)C5—C10—H10119.00
C6—C7—C8120.7 (3)C9—C10—H10119.00
C7—C8—C9117.5 (3)C8—C11—H11108.00
C7—C8—C11121.2 (3)C12—C11—H11108.00
C9—C8—C11121.2 (3)C13—C11—H11108.00
C8—C9—C10120.8 (3)C11—C12—H12A110.00
C5—C10—C9122.1 (3)C11—C12—H12B110.00
C8—C11—C12110.9 (3)C11—C12—H12C109.00
C8—C11—C13109.8 (3)H12A—C12—H12B109.00
C12—C11—C13110.8 (3)H12A—C12—H12C109.00
O1—C13—N1121.1 (4)H12B—C12—H12C109.00
O1—C13—C11121.1 (3)N1—C14—H14A110.00
N1—C13—C11117.8 (3)N1—C14—H14B110.00
N1—C14—C15109.1 (3)C15—C14—H14A110.00
O2—C15—C14111.4 (3)C15—C14—H14B110.00
O2—C16—C17111.6 (3)H14A—C14—H14B108.00
N1—C17—C16109.8 (3)O2—C15—H15A109.00
C2—C1—H1A110.00O2—C15—H15B109.00
C2—C1—H1B109.00C14—C15—H15A109.00
C2—C1—H1C109.00C14—C15—H15B109.00
H1A—C1—H1B110.00H15A—C15—H15B108.00
H1A—C1—H1C109.00O2—C16—H16A109.00
H1B—C1—H1C109.00O2—C16—H16B109.00
C1—C2—H2108.00C17—C16—H16A109.00
C3—C2—H2108.00C17—C16—H16B109.00
C4—C2—H2108.00H16A—C16—H16B108.00
C2—C3—H3A109.00N1—C17—H17A110.00
C2—C3—H3B109.00N1—C17—H17B110.00
C2—C3—H3C110.00C16—C17—H17A110.00
H3A—C3—H3B109.00C16—C17—H17B110.00
H3A—C3—H3C109.00H17A—C17—H17B108.00
H3B—C3—H3C109.00
C16—O2—C15—C1460.7 (4)C6—C5—C10—C91.2 (5)
C15—O2—C16—C1758.9 (4)C5—C6—C7—C81.1 (6)
C14—N1—C13—O16.0 (4)C6—C7—C8—C90.3 (5)
C14—N1—C13—C11170.6 (3)C6—C7—C8—C11176.6 (3)
C17—N1—C13—O1179.1 (3)C7—C8—C9—C101.0 (5)
C17—N1—C13—C112.5 (4)C11—C8—C9—C10176.0 (3)
C13—N1—C14—C15119.2 (3)C7—C8—C11—C1278.8 (4)
C17—N1—C14—C1554.9 (3)C7—C8—C11—C1343.9 (4)
C13—N1—C17—C16120.0 (4)C9—C8—C11—C1298.0 (4)
C14—N1—C17—C1653.6 (4)C9—C8—C11—C13139.3 (3)
C1—C2—C4—C5167.1 (3)C8—C9—C10—C50.2 (6)
C3—C2—C4—C568.2 (4)C8—C11—C13—O1100.5 (3)
C2—C4—C5—C693.4 (4)C8—C11—C13—N176.1 (3)
C2—C4—C5—C1085.9 (4)C12—C11—C13—O122.4 (4)
C4—C5—C6—C7177.4 (4)C12—C11—C13—N1161.0 (3)
C10—C5—C6—C71.9 (6)N1—C14—C15—O258.2 (4)
C4—C5—C10—C9178.1 (3)O2—C16—C17—N155.1 (4)

Experimental details

Crystal data
Chemical formulaC17H25NO2
Mr275.38
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)14.1389 (19), 10.3358 (15), 11.3552 (15)
β (°) 103.426 (8)
V3)1614.1 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.32 × 0.14 × 0.12
Data collection
DiffractometerBruker Kappa APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.977, 0.990
No. of measured, independent and
observed [I > 2σ(I)] reflections
11200, 2835, 1246
Rint0.100
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.062, 0.159, 0.98
No. of reflections2835
No. of parameters185
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.17, 0.16

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

 

Acknowledgements

The authors acknowledge the provision of funds for the purchase of the diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan. The authors also acknowledge the technical support provided by Syed Muhammad Hussain Rizvi of Bana Inter­national, Karachi, Pakistan.

References

First citationBruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationBruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals
First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals
First citationHansen, L. K., Perlovich, G. L. & Bauer-Brandl, A. (2003). Acta Cryst. E59, o1357–o1358.  CSD CrossRef IUCr Journals
First citationNasirullah, Islam, N. U., Tahir, M. N., Khan, I. & Zulfiqar, M. (2012). Acta Cryst. E68, o2636.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals

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