N-(4-Chloro­phen­yl)-4-(2-oxocyclo­pent­yl)butyramide

Yu, L.-T.; Wei, J.-T.; Zhou, X.-G.

doi:10.1107/S1600536808042505

organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page o162

doi:10.1107/S1600536808042505

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N-(4-Chlorophenyl)-4-(2-oxocyclopentyl)butyramide

Lin-Tao Yu,^a Jiang-Tao Wei ^a and Xiang-Ge Zhou ^a ^*

^aInstitute of Homogeneous Catalysis, Department of Chemistry, Sichuan University, Chengdu 610064, People's Republic of China
^*Correspondence e-mail: scuzhou106@yahoo.com.cn

(Received 12 December 2008; accepted 13 December 2008; online 20 December 2008)

In the title compound, C₁₅H₁₈ClNO₂, the amide group is coplanar with the chlorophenyl group, making a dihedral angle of 1.71 (12)°. The cyclopentanone ring adopts a twist conformation. A weak intramolecular C—H⋯O hydrogen bond is observed. Molecules are linked into cyclic centrosymmetric dimers by paired N—H⋯O hydrogen bonds.

Related literature

For the synthesis of cyathin terpenoids, see: Drège et al. (2006 ).

Experimental

Crystal data

C₁₅H₁₈ClNO₂
M_r = 279.75
Triclinic, $[P \overline 1]$
a = 5.5897 (2) Å
b = 8.8847 (3) Å
c = 14.6480 (4) Å
α = 80.906 (2)°
β = 86.436 (2)°
γ = 85.351 (2)°
V = 715.05 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 296 (2) K
0.42 × 0.40 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.895, T_max = 0.948
8899 measured reflections
3273 independent reflections
1648 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.147
S = 1.01
3273 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.86	2.17	2.980 (2)	158
C15—H15⋯O2	0.93	2.29	2.889 (2)	121
Symmetry code: (i) -x, -y+2, -z+1.

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808042505/ci2743sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808042505/ci2743Isup2.hkl

checkCIF report

Comment top

2-Oxocyclopentyl carboxylic acid derivatives are a class of starting materials important for the preparation of cyathin terpenoids (Drège et al., 2006). We report here the crystal structure of the title compound, a oxocyclopentyl derivative.

Bond lengths and angles are normal. The amide group is almost coplanar with the benzene ring system (Fig. 1). The C8/C9/N1/O2 and C10—C15 planes form dihedral angle of 1.71 (12)°. The cyclopentanone ring adopts a twist conformation. An intramolecular C15—H15···O2 hydrogen bond is observed.

The crystal packing is stabilized by N—H···O hydrogen bonds (Table 1). The molecules are linked into cyclic centrosymmetric dimers by paired N—H···O hydrogen bonds.

Related literature top

For the synthesis of cyathin terpenoids, see: Drège et al. (2006).

Experimental top

A mixture of spiro[4,4]nonane-1,6-dione (1 mmol), p-chloroaniline (2.2 mmol) and iodine (0.1 mmol) was stirred in refluxing dichloromethane (20 ml) for 24 h to afford the title compound. Single crystals suitable for X-ray diffraction were obtained by slow evaporation an ethyl acetate solution.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atomic numbering. H atoms have been omitted for clarity.

N-(4-Chlorophenyl)-4-(2-oxocyclopentyl)butyramide top

Crystal data top

C₁₅H₁₈ClNO₂	Z = 2
M_r = 279.75	F(000) = 296
Triclinic, P1	D_x = 1.299 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.5897 (2) Å	Cell parameters from 2436 reflections
b = 8.8847 (3) Å	θ = 2.8–25.4°
c = 14.6480 (4) Å	µ = 0.27 mm⁻¹
α = 80.906 (2)°	T = 296 K
β = 86.436 (2)°	Plate, colourless
γ = 85.351 (2)°	0.42 × 0.40 × 0.20 mm
V = 715.05 (4) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	3273 independent reflections
Radiation source: fine-focus sealed tube	1648 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
ϕ and ω scans	θ_max = 27.5°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −7→7
T_min = 0.895, T_max = 0.948	k = −11→11
8899 measured reflections	l = −18→18

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.147	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0664P)²] where P = (F_o² + 2F_c²)/3
3273 reflections	(Δ/σ)_max = 0.001
172 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₅H₁₈ClNO₂	γ = 85.351 (2)°
M_r = 279.75	V = 715.05 (4) Å³
Triclinic, P1	Z = 2
a = 5.5897 (2) Å	Mo Kα radiation
b = 8.8847 (3) Å	µ = 0.27 mm⁻¹
c = 14.6480 (4) Å	T = 296 K
α = 80.906 (2)°	0.42 × 0.40 × 0.20 mm
β = 86.436 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3273 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1648 reflections with I > 2σ(I)
T_min = 0.895, T_max = 0.948	R_int = 0.047
8899 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.147	H-atom parameters constrained
S = 1.01	Δρ_max = 0.35 e Å⁻³
3273 reflections	Δρ_min = −0.21 e Å⁻³
172 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

	x	y	z	U_iso*/U_eq
Cl1	1.27737 (9)	0.49407 (7)	0.08887 (3)	0.06892 (18)
O1	−0.2238 (3)	1.05919 (19)	0.73712 (11)	0.0902 (5)
O2	0.7274 (3)	0.6356 (2)	0.50469 (10)	0.0867 (5)
N1	0.5659 (3)	0.70953 (19)	0.36547 (10)	0.0563 (5)
H1N	0.4405	0.7567	0.3402	0.068*
C1	−0.0587 (4)	0.9846 (2)	0.77649 (14)	0.0629 (6)
C2	−0.0494 (4)	0.9474 (3)	0.87916 (14)	0.0796 (8)
H2A	−0.1708	0.8781	0.9045	0.095*
H2B	−0.0749	1.0394	0.9075	0.095*
C3	0.2010 (4)	0.8723 (3)	0.89563 (15)	0.0833 (8)
H3A	0.1979	0.7899	0.9477	0.100*
H3B	0.3091	0.9461	0.9077	0.100*
C4	0.2785 (4)	0.8112 (3)	0.80617 (14)	0.0780 (7)
H4A	0.4521	0.8053	0.7971	0.094*
H4B	0.2232	0.7101	0.8075	0.094*
C5	0.1666 (4)	0.9211 (3)	0.73132 (14)	0.0690 (7)
H5	0.2718	1.0058	0.7195	0.083*
C6	0.1382 (3)	0.8771 (2)	0.63830 (13)	0.0604 (6)
H6A	0.0857	0.9677	0.5962	0.072*
H6B	0.0131	0.8062	0.6438	0.072*
C7	0.3644 (4)	0.8047 (3)	0.59707 (14)	0.0640 (6)
H7A	0.4926	0.8726	0.5956	0.077*
H7B	0.4106	0.7102	0.6369	0.077*
C8	0.3397 (4)	0.7707 (3)	0.50060 (13)	0.0643 (6)
H8A	0.2114	0.7029	0.5022	0.077*
H8B	0.2928	0.8653	0.4610	0.077*
C9	0.5627 (3)	0.6992 (2)	0.45871 (13)	0.0569 (6)
C10	0.7424 (3)	0.6552 (2)	0.30324 (12)	0.0480 (5)
C11	0.6974 (3)	0.6867 (2)	0.21012 (13)	0.0567 (6)
H11	0.5551	0.7414	0.1916	0.068*
C12	0.8597 (3)	0.6383 (2)	0.14440 (13)	0.0583 (6)
H12	0.8272	0.6598	0.0820	0.070*
C13	1.0715 (4)	0.5576 (2)	0.17201 (13)	0.0541 (5)
C14	1.1172 (3)	0.5254 (2)	0.26439 (13)	0.0573 (6)
H14	1.2602	0.4712	0.2826	0.069*
C15	0.9538 (3)	0.5726 (2)	0.33070 (13)	0.0544 (5)
H15	0.9854	0.5491	0.3931	0.065*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0568 (3)	0.0872 (4)	0.0638 (3)	0.0107 (3)	0.0032 (2)	−0.0254 (3)
O1	0.0787 (10)	0.1028 (12)	0.0828 (10)	0.0400 (9)	−0.0128 (8)	−0.0151 (9)
O2	0.0723 (10)	0.1230 (13)	0.0595 (9)	0.0368 (10)	−0.0164 (8)	−0.0149 (9)
N1	0.0465 (9)	0.0684 (11)	0.0526 (9)	0.0090 (8)	−0.0091 (7)	−0.0088 (8)
C1	0.0598 (12)	0.0642 (14)	0.0629 (12)	0.0108 (11)	−0.0048 (10)	−0.0112 (11)
C2	0.0792 (15)	0.0972 (18)	0.0594 (13)	0.0053 (14)	0.0041 (12)	−0.0120 (13)
C3	0.0906 (17)	0.1014 (19)	0.0553 (12)	0.0122 (15)	−0.0159 (12)	−0.0090 (13)
C4	0.0749 (15)	0.0888 (17)	0.0686 (14)	0.0144 (13)	−0.0177 (12)	−0.0118 (13)
C5	0.0677 (13)	0.0778 (15)	0.0586 (12)	0.0218 (12)	−0.0071 (11)	−0.0137 (12)
C6	0.0537 (12)	0.0688 (14)	0.0581 (11)	0.0089 (11)	−0.0066 (10)	−0.0132 (11)
C7	0.0566 (12)	0.0726 (15)	0.0634 (12)	0.0057 (11)	−0.0043 (10)	−0.0173 (11)
C8	0.0556 (12)	0.0810 (15)	0.0556 (12)	0.0094 (11)	−0.0046 (10)	−0.0148 (11)
C9	0.0502 (11)	0.0674 (14)	0.0524 (11)	0.0056 (11)	−0.0091 (10)	−0.0096 (10)
C10	0.0442 (10)	0.0490 (12)	0.0512 (10)	0.0003 (9)	−0.0041 (9)	−0.0102 (9)
C11	0.0497 (11)	0.0652 (13)	0.0543 (11)	0.0058 (10)	−0.0097 (9)	−0.0091 (10)
C12	0.0577 (12)	0.0693 (14)	0.0482 (11)	0.0029 (11)	−0.0078 (9)	−0.0117 (10)
C13	0.0524 (11)	0.0540 (12)	0.0572 (11)	−0.0021 (10)	0.0000 (9)	−0.0144 (10)
C14	0.0513 (11)	0.0565 (13)	0.0634 (12)	0.0066 (10)	−0.0109 (10)	−0.0094 (11)
C15	0.0527 (11)	0.0596 (13)	0.0505 (11)	0.0003 (10)	−0.0084 (9)	−0.0074 (10)

Geometric parameters (Å, º) top

Cl1—C13	1.750 (2)	C6—C7	1.508 (3)
O1—C1	1.212 (2)	C6—H6A	0.97
O2—C9	1.222 (2)	C6—H6B	0.97
N1—C9	1.353 (2)	C7—C8	1.508 (3)
N1—C10	1.410 (2)	C7—H7A	0.97
N1—H1N	0.86	C7—H7B	0.97
C1—C2	1.491 (3)	C8—C9	1.495 (3)
C1—C5	1.497 (3)	C8—H8A	0.97
C2—C3	1.517 (3)	C8—H8B	0.97
C2—H2A	0.97	C10—C11	1.383 (2)
C2—H2B	0.97	C10—C15	1.386 (2)
C3—C4	1.522 (3)	C11—C12	1.376 (3)
C3—H3A	0.97	C11—H11	0.93
C3—H3B	0.97	C12—C13	1.382 (3)
C4—C5	1.481 (3)	C12—H12	0.93
C4—H4A	0.97	C13—C14	1.374 (3)
C4—H4B	0.97	C14—C15	1.382 (3)
C5—C6	1.496 (3)	C14—H14	0.93
C5—H5	0.98	C15—H15	0.93

C9—N1—C10	130.17 (15)	H6A—C6—H6B	107.7
C9—N1—H1N	114.9	C8—C7—C6	113.75 (16)
C10—N1—H1N	114.9	C8—C7—H7A	108.8
O1—C1—C2	123.9 (2)	C6—C7—H7A	108.8
O1—C1—C5	126.11 (19)	C8—C7—H7B	108.8
C2—C1—C5	110.00 (17)	C6—C7—H7B	108.8
C1—C2—C3	104.75 (17)	H7A—C7—H7B	107.7
C1—C2—H2A	110.8	C9—C8—C7	114.38 (16)
C3—C2—H2A	110.8	C9—C8—H8A	108.7
C1—C2—H2B	110.8	C7—C8—H8A	108.7
C3—C2—H2B	110.8	C9—C8—H8B	108.7
H2A—C2—H2B	108.9	C7—C8—H8B	108.7
C2—C3—C4	104.48 (17)	H8A—C8—H8B	107.6
C2—C3—H3A	110.9	O2—C9—N1	122.76 (18)
C4—C3—H3A	110.9	O2—C9—C8	122.95 (18)
C2—C3—H3B	110.9	N1—C9—C8	114.29 (16)
C4—C3—H3B	110.9	C11—C10—C15	119.36 (18)
H3A—C3—H3B	108.9	C11—C10—N1	117.04 (16)
C5—C4—C3	105.72 (18)	C15—C10—N1	123.60 (16)
C5—C4—H4A	110.6	C12—C11—C10	121.07 (18)
C3—C4—H4A	110.6	C12—C11—H11	119.5
C5—C4—H4B	110.6	C10—C11—H11	119.5
C3—C4—H4B	110.6	C11—C12—C13	119.37 (18)
H4A—C4—H4B	108.7	C11—C12—H12	120.3
C4—C5—C6	120.96 (19)	C13—C12—H12	120.3
C4—C5—C1	104.34 (17)	C14—C13—C12	119.93 (18)
C6—C5—C1	115.15 (17)	C14—C13—Cl1	120.45 (15)
C4—C5—H5	105.0	C12—C13—Cl1	119.61 (15)
C6—C5—H5	105.0	C13—C14—C15	120.91 (18)
C1—C5—H5	105.0	C13—C14—H14	119.5
C5—C6—C7	113.96 (16)	C15—C14—H14	119.5
C5—C6—H6A	108.8	C14—C15—C10	119.36 (17)
C7—C6—H6A	108.8	C14—C15—H15	120.3
C5—C6—H6B	108.8	C10—C15—H15	120.3
C7—C6—H6B	108.8

O1—C1—C2—C3	−172.7 (2)	C10—N1—C9—C8	−179.45 (18)
C5—C1—C2—C3	5.5 (3)	C7—C8—C9—O2	19.1 (3)
C1—C2—C3—C4	−23.3 (3)	C7—C8—C9—N1	−161.51 (18)
C2—C3—C4—C5	33.3 (3)	C9—N1—C10—C11	−178.43 (19)
C3—C4—C5—C6	−161.1 (2)	C9—N1—C10—C15	2.0 (3)
C3—C4—C5—C1	−29.4 (2)	C15—C10—C11—C12	−0.5 (3)
O1—C1—C5—C4	−166.9 (2)	N1—C10—C11—C12	179.91 (18)
C2—C1—C5—C4	14.9 (3)	C10—C11—C12—C13	−0.3 (3)
O1—C1—C5—C6	−32.0 (3)	C11—C12—C13—C14	0.5 (3)
C2—C1—C5—C6	149.9 (2)	C11—C12—C13—Cl1	179.36 (16)
C4—C5—C6—C7	−49.6 (3)	C12—C13—C14—C15	0.1 (3)
C1—C5—C6—C7	−176.49 (18)	Cl1—C13—C14—C15	−178.77 (15)
C5—C6—C7—C8	−175.97 (19)	C13—C14—C15—C10	−0.9 (3)
C6—C7—C8—C9	179.88 (18)	C11—C10—C15—C14	1.0 (3)
C10—N1—C9—O2	0.0 (3)	N1—C10—C15—C14	−179.37 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.86	2.17	2.980 (2)	158
C15—H15···O2	0.93	2.29	2.889 (2)	121

Symmetry code: (i) −x, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₈ClNO₂
M_r	279.75
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	5.5897 (2), 8.8847 (3), 14.6480 (4)
α, β, γ (°)	80.906 (2), 86.436 (2), 85.351 (2)
V (Å³)	715.05 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.42 × 0.40 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.895, 0.948
No. of measured, independent and observed [I > 2σ(I)] reflections	8899, 3273, 1648
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.147, 1.01
No. of reflections	3273
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.21

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.86	2.17	2.980 (2)	158
C15—H15···O2	0.93	2.29	2.889 (2)	121

Symmetry code: (i) −x, −y+2, −z+1.

Acknowledgements

The authors thank the NSFC (grant Nos. 20672075 and 20771076) and Sichuan University for financial support.

References

Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Drège, E., Tominiaux, C., Morgant, G. & Desmaële, D. (2006). Eur. J. Org. Chem. pp. 4825–4840. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar