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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2012 Aug 4;68(Pt 9):o2637. doi: 10.1107/S1600536812033442

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

Nasirullah a, Nazar Ul Islam a, M Nawaz Tahir b,*, Ikhtiar Khan a, Muhammad Zulfiqar b
PMCID: PMC3435664  PMID: 22969537

Abstract

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 ▶); Nasirullah et al. (2012 ▶).graphic file with name e-68-o2637-scheme1.jpg

Experimental  

Crystal data  

  • C17H25NO2

  • M r = 275.38

  • Monoclinic, Inline graphic

  • 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 ▶) T min = 0.977, T max = 0.990

  • 11200 measured reflections

  • 2835 independent reflections

  • 1246 reflections with I > 2σ(I)

  • R int = 0.100

Refinement  

  • R[F 2 > 2σ(F 2)] = 0.062

  • wR(F 2) = 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 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; 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 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812033442/wn2484sup1.cif

e-68-o2637-sup1.cif (24.4KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812033442/wn2484Isup2.hkl

e-68-o2637-Isup2.hkl (136.4KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536812033442/wn2484Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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.

supplementary crystallographic information

Comment

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.

Experimental

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

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.

Figures

Fig. 1.

Fig. 1.

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View of the title compound with displacement ellipsoids drawn at the 50% probability level. Hydrogen atoms are shown as spheres of arbitrary radius.

Crystal data

C17H25NO2 F(000) = 600
Mr = 275.38 Dx = 1.133 Mg m−3
Monoclinic, P21/c Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc Cell parameters from 1246 reflections
a = 14.1389 (19) Å θ = 1.5–25.0°
b = 10.3358 (15) Å µ = 0.07 mm−1
c = 11.3552 (15) Å T = 296 K
β = 103.426 (8)° Needle, white
V = 1614.1 (4) Å3 0.32 × 0.14 × 0.12 mm
Z = 4
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Data collection

Bruker Kappa APEXII CCD diffractometer 2835 independent reflections
Radiation source: fine-focus sealed tube 1246 reflections with I > 2σ(I)
Graphite monochromator Rint = 0.100
Detector resolution: 8.20 pixels mm-1 θmax = 25.0°, θmin = 1.5°
ω scans h = −16→16
Absorption correction: multi-scan (SADABS; Bruker, 2005) k = −12→12
Tmin = 0.977, Tmax = 0.990 l = −13→13
11200 measured reflections
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Refinement

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)] = 0.062 H-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 reflections Δρmax = 0.17 e Å−3
185 parameters Δρmin = −0.16 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: 0.0053 (13)
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Special details

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

x y z Uiso*/Ueq
O1 0.35601 (17) 0.2845 (2) 0.5282 (2) 0.0581 (10)
O2 0.61970 (19) 0.4915 (2) 0.7983 (2) 0.0731 (12)
N1 0.4656 (2) 0.3220 (2) 0.7033 (2) 0.0433 (10)
C1 0.0388 (3) 0.9627 (4) 0.8327 (4) 0.097 (2)
C2 0.0646 (3) 0.8359 (3) 0.7788 (3) 0.0655 (17)
C3 0.0182 (3) 0.8282 (4) 0.6453 (4) 0.098 (2)
C4 0.1743 (3) 0.8188 (3) 0.8061 (3) 0.0567 (17)
C5 0.2088 (2) 0.6854 (3) 0.7822 (3) 0.0437 (12)
C6 0.2300 (3) 0.6539 (3) 0.6736 (3) 0.0567 (16)
C7 0.2579 (3) 0.5313 (3) 0.6491 (3) 0.0540 (14)
C8 0.2674 (2) 0.4342 (3) 0.7350 (3) 0.0374 (12)
C9 0.2484 (2) 0.4655 (3) 0.8451 (3) 0.0464 (12)
C10 0.2196 (3) 0.5887 (3) 0.8674 (3) 0.0497 (14)
C11 0.2928 (2) 0.2963 (3) 0.7066 (3) 0.0406 (12)
C12 0.2036 (3) 0.2257 (4) 0.6335 (3) 0.0656 (17)
C13 0.3738 (3) 0.2981 (3) 0.6387 (3) 0.0429 (14)
C14 0.5436 (3) 0.3446 (3) 0.6411 (3) 0.0536 (14)
C15 0.5844 (3) 0.4767 (3) 0.6721 (3) 0.0636 (17)
C16 0.5431 (3) 0.4735 (4) 0.8584 (3) 0.0660 (16)
C17 0.4977 (3) 0.3419 (3) 0.8333 (3) 0.0467 (12)
H1A −0.03054 0.97255 0.81480 0.1454*
H1B 0.06708 1.03365 0.79843 0.1454*
H1C 0.06382 0.96156 0.91889 0.1454*
H2 0.03796 0.76513 0.81872 0.0784*
H3A 0.03562 0.74781 0.61355 0.1464*
H3B 0.04078 0.89886 0.60416 0.1464*
H3C −0.05117 0.83309 0.63303 0.1464*
H4A 0.20066 0.88050 0.75783 0.0682*
H4B 0.20075 0.83986 0.89056 0.0682*
H6 0.22532 0.71765 0.61471 0.0681*
H7 0.27059 0.51341 0.57397 0.0647*
H9 0.25507 0.40278 0.90515 0.0556*
H10 0.20703 0.60694 0.94248 0.0595*
H11 0.31628 0.25010 0.78316 0.0487*
H12A 0.22052 0.13788 0.61992 0.0984*
H12B 0.18077 0.26834 0.55704 0.0984*
H12C 0.15319 0.22633 0.67745 0.0984*
H14A 0.51844 0.33736 0.55428 0.0646*
H14B 0.59422 0.28019 0.66586 0.0646*
H15A 0.63699 0.49156 0.63191 0.0764*
H15B 0.53433 0.54068 0.64276 0.0764*
H16A 0.49383 0.53924 0.83179 0.0792*
H16B 0.56830 0.48364 0.94496 0.0792*
H17A 0.54465 0.27592 0.86816 0.0561*
H17B 0.44261 0.33479 0.87038 0.0561*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
O1 0.0606 (18) 0.0754 (18) 0.0365 (15) −0.0023 (14) 0.0078 (12) −0.0122 (12)
O2 0.069 (2) 0.079 (2) 0.076 (2) −0.0311 (16) 0.0263 (16) −0.0203 (15)
N1 0.0424 (19) 0.0540 (19) 0.0348 (16) −0.0021 (15) 0.0119 (15) −0.0046 (13)
C1 0.082 (4) 0.076 (3) 0.130 (4) 0.031 (3) 0.018 (3) −0.027 (3)
C2 0.053 (3) 0.057 (3) 0.084 (3) 0.011 (2) 0.011 (2) −0.005 (2)
C3 0.077 (4) 0.111 (4) 0.090 (3) 0.027 (3) −0.011 (3) −0.020 (3)
C4 0.056 (3) 0.054 (3) 0.059 (3) 0.001 (2) 0.011 (2) −0.0066 (18)
C5 0.041 (2) 0.046 (2) 0.046 (2) 0.0025 (18) 0.0137 (18) −0.0063 (19)
C6 0.072 (3) 0.044 (2) 0.058 (3) 0.015 (2) 0.023 (2) 0.0139 (18)
C7 0.074 (3) 0.054 (2) 0.038 (2) 0.011 (2) 0.0209 (19) 0.0030 (19)
C8 0.036 (2) 0.042 (2) 0.035 (2) 0.0020 (16) 0.0101 (15) −0.0018 (16)
C9 0.052 (2) 0.048 (2) 0.040 (2) 0.0067 (19) 0.0123 (18) 0.0058 (17)
C10 0.059 (3) 0.055 (2) 0.037 (2) 0.003 (2) 0.0149 (18) −0.0054 (19)
C11 0.039 (2) 0.041 (2) 0.042 (2) 0.0008 (17) 0.0099 (17) −0.0021 (16)
C12 0.049 (3) 0.068 (3) 0.078 (3) −0.010 (2) 0.011 (2) −0.018 (2)
C13 0.049 (3) 0.040 (2) 0.040 (2) 0.0022 (18) 0.0108 (19) −0.0050 (16)
C14 0.047 (2) 0.068 (3) 0.051 (2) −0.003 (2) 0.022 (2) −0.0057 (19)
C15 0.067 (3) 0.065 (3) 0.066 (3) −0.007 (2) 0.030 (2) 0.006 (2)
C16 0.071 (3) 0.074 (3) 0.057 (2) −0.020 (2) 0.023 (2) −0.019 (2)
C17 0.048 (2) 0.054 (2) 0.038 (2) −0.0046 (18) 0.0096 (17) 0.0034 (16)
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Geometric parameters (Å, º)

O1—C13 1.229 (4) C1—H1C 0.9600
O2—C15 1.412 (4) C2—H2 0.9800
O2—C16 1.420 (5) C3—H3A 0.9600
N1—C13 1.357 (5) C3—H3B 0.9600
N1—C14 1.460 (5) C3—H3C 0.9600
N1—C17 1.455 (4) C4—H4A 0.9700
C1—C2 1.526 (5) C4—H4B 0.9700
C2—C3 1.508 (6) C6—H6 0.9300
C2—C4 1.520 (6) C7—H7 0.9300
C4—C5 1.508 (5) C9—H9 0.9300
C5—C6 1.374 (5) C10—H10 0.9300
C5—C10 1.375 (5) C11—H11 0.9800
C6—C7 1.375 (5) C12—H12A 0.9600
C7—C8 1.384 (5) C12—H12B 0.9600
C8—C9 1.377 (5) C12—H12C 0.9600
C8—C11 1.523 (4) C14—H14A 0.9700
C9—C10 1.378 (5) C14—H14B 0.9700
C11—C12 1.525 (5) C15—H15A 0.9700
C11—C13 1.522 (5) C15—H15B 0.9700
C14—C15 1.492 (5) C16—H16A 0.9700
C16—C17 1.503 (5) C16—H16B 0.9700
C1—H1A 0.9600 C17—H17A 0.9700
C1—H1B 0.9600 C17—H17B 0.9700
C15—O2—C16 110.1 (3) C2—C4—H4A 108.00
C13—N1—C14 120.2 (3) C2—C4—H4B 108.00
C13—N1—C17 127.5 (3) C5—C4—H4A 108.00
C14—N1—C17 112.1 (3) C5—C4—H4B 108.00
C1—C2—C3 111.1 (3) H4A—C4—H4B 108.00
C1—C2—C4 110.2 (3) C5—C6—H6 119.00
C3—C2—C4 112.6 (3) C7—C6—H6 119.00
C2—C4—C5 115.3 (3) C6—C7—H7 120.00
C4—C5—C6 121.7 (3) C8—C7—H7 120.00
C4—C5—C10 121.7 (3) C8—C9—H9 120.00
C6—C5—C10 116.6 (3) C10—C9—H9 120.00
C5—C6—C7 122.2 (3) C5—C10—H10 119.00
C6—C7—C8 120.7 (3) C9—C10—H10 119.00
C7—C8—C9 117.5 (3) C8—C11—H11 108.00
C7—C8—C11 121.2 (3) C12—C11—H11 108.00
C9—C8—C11 121.2 (3) C13—C11—H11 108.00
C8—C9—C10 120.8 (3) C11—C12—H12A 110.00
C5—C10—C9 122.1 (3) C11—C12—H12B 110.00
C8—C11—C12 110.9 (3) C11—C12—H12C 109.00
C8—C11—C13 109.8 (3) H12A—C12—H12B 109.00
C12—C11—C13 110.8 (3) H12A—C12—H12C 109.00
O1—C13—N1 121.1 (4) H12B—C12—H12C 109.00
O1—C13—C11 121.1 (3) N1—C14—H14A 110.00
N1—C13—C11 117.8 (3) N1—C14—H14B 110.00
N1—C14—C15 109.1 (3) C15—C14—H14A 110.00
O2—C15—C14 111.4 (3) C15—C14—H14B 110.00
O2—C16—C17 111.6 (3) H14A—C14—H14B 108.00
N1—C17—C16 109.8 (3) O2—C15—H15A 109.00
C2—C1—H1A 110.00 O2—C15—H15B 109.00
C2—C1—H1B 109.00 C14—C15—H15A 109.00
C2—C1—H1C 109.00 C14—C15—H15B 109.00
H1A—C1—H1B 110.00 H15A—C15—H15B 108.00
H1A—C1—H1C 109.00 O2—C16—H16A 109.00
H1B—C1—H1C 109.00 O2—C16—H16B 109.00
C1—C2—H2 108.00 C17—C16—H16A 109.00
C3—C2—H2 108.00 C17—C16—H16B 109.00
C4—C2—H2 108.00 H16A—C16—H16B 108.00
C2—C3—H3A 109.00 N1—C17—H17A 110.00
C2—C3—H3B 109.00 N1—C17—H17B 110.00
C2—C3—H3C 110.00 C16—C17—H17A 110.00
H3A—C3—H3B 109.00 C16—C17—H17B 110.00
H3A—C3—H3C 109.00 H17A—C17—H17B 108.00
H3B—C3—H3C 109.00
C16—O2—C15—C14 −60.7 (4) C6—C5—C10—C9 −1.2 (5)
C15—O2—C16—C17 58.9 (4) C5—C6—C7—C8 −1.1 (6)
C14—N1—C13—O1 6.0 (4) C6—C7—C8—C9 −0.3 (5)
C14—N1—C13—C11 −170.6 (3) C6—C7—C8—C11 176.6 (3)
C17—N1—C13—O1 179.1 (3) C7—C8—C9—C10 1.0 (5)
C17—N1—C13—C11 2.5 (4) C11—C8—C9—C10 −176.0 (3)
C13—N1—C14—C15 119.2 (3) C7—C8—C11—C12 −78.8 (4)
C17—N1—C14—C15 −54.9 (3) C7—C8—C11—C13 43.9 (4)
C13—N1—C17—C16 −120.0 (4) C9—C8—C11—C12 98.0 (4)
C14—N1—C17—C16 53.6 (4) C9—C8—C11—C13 −139.3 (3)
C1—C2—C4—C5 167.1 (3) C8—C9—C10—C5 −0.2 (6)
C3—C2—C4—C5 −68.2 (4) C8—C11—C13—O1 −100.5 (3)
C2—C4—C5—C6 93.4 (4) C8—C11—C13—N1 76.1 (3)
C2—C4—C5—C10 −85.9 (4) C12—C11—C13—O1 22.4 (4)
C4—C5—C6—C7 −177.4 (4) C12—C11—C13—N1 −161.0 (3)
C10—C5—C6—C7 1.9 (6) N1—C14—C15—O2 58.2 (4)
C4—C5—C10—C9 178.1 (3) O2—C16—C17—N1 −55.1 (4)
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WN2484).

References

  1. Bruker (2005). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  2. Bruker (2009). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  3. Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
  4. Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.
  5. Hansen, L. K., Perlovich, G. L. & Bauer-Brandl, A. (2003). Acta Cryst. E59, o1357–o1358.
  6. Nasirullah, Islam, N. U., Tahir, M. N., Khan, I. & Zulfiqar, M. (2012). Acta Cryst. E68, o2636. [DOI] [PMC free article] [PubMed]
  7. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  8. Spek, A. L. (2009). Acta Cryst. D65, 148–155. [DOI] [PMC free article] [PubMed]

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812033442/wn2484sup1.cif

e-68-o2637-sup1.cif (24.4KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812033442/wn2484Isup2.hkl

e-68-o2637-Isup2.hkl (136.4KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536812033442/wn2484Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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