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

Nasirullah; Islam, N.U.; Tahir, M.N.; Khan, I.; Zulfiqar, M.

doi:10.1107/S1600536812033442

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page o2637

doi:10.1107/S1600536812033442

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

Nasirullah,^a Nazar Ul Islam,^a M. Nawaz Tahir,^b ^* Ikhtiar Khan ^a and Muhammad Zulfiqar ^b

^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 ); Nasirullah et al. (2012 ).

Experimental

Crystal data

C₁₇H₂₅NO₂
M_r = 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 ) 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[F² > 2σ(F²)] = 0.062
wR(F²) = 0.159
S = 0.98
2835 reflections
185 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −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).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812033442/wn2484sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812033442/wn2484Isup3.cml

checkCIF report

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%.

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

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

C₁₇H₂₅NO₂	F(000) = 600
M_r = 275.38	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0542P)²] where P = (F_o² + 2F_c²)/3
S = 0.98	(Δ/σ)_max < 0.001
2835 reflections	Δρ_max = 0.17 e Å⁻³
185 parameters	Δρ_min = −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)

Crystal data top

C₁₇H₂₅NO₂	V = 1614.1 (4) Å³
M_r = 275.38	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.1389 (19) Å	µ = 0.07 mm⁻¹
b = 10.3358 (15) Å	T = 296 K
c = 11.3552 (15) Å	0.32 × 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)
T_min = 0.977, T_max = 0.990	R_int = 0.100
11200 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	1 restraint
wR(F²) = 0.159	H-atom parameters constrained
S = 0.98	Δρ_max = 0.17 e Å⁻³
2835 reflections	Δρ_min = −0.16 e Å⁻³
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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₁₇H₂₅NO₂
M_r	275.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	14.1389 (19), 10.3358 (15), 11.3552 (15)
β (°)	103.426 (8)
V (Å³)	1614.1 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.32 × 0.14 × 0.12

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.977, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	11200, 2835, 1246
R_int	0.100
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.159, 0.98
No. of reflections	2835
No. of parameters	185
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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

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