(Anthracen-9-yl)(piperidin-1-yl)­methanone

Hu, H.-Y.; Huang, Y.-C.; Yu, H.-T.; Zhang, Y.

doi:10.1107/S1600536808033205

organic compounds

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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2120

doi:10.1107/S1600536808033205

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(Anthracen-9-yl)(piperidin-1-yl)methanone

Hua-You Hu,^a ^* Yu-Cheng Huang,^b Hai-Tao Yu ^b and Yan Zhang ^b

^aDepartment of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, People's Republic of China, and ^bSchool of Chemistry and Chemical Engineering, Key Laboratory of Analytical Chemistry for Life Science, Ministry of Education, Nanjing University, Nanjing 210093, People's Republic of China
^*Correspondence e-mail: huayouhu@seu.edu.cn

(Received 5 September 2008; accepted 13 October 2008; online 15 October 2008)

The title compound, C₂₀H₁₉NO, is a substructure of CP-640186, a potent inhibitor of mammalian acetyl-coenzyme A carboxylases. In the crystal structure, the amide group forms a dihedral angle of 87.0 (1)° with the plane of the anthracene unit and the piperidine ring adopts a chair conformation. Molecules are arranged into layers parallel to (100) and adjacent anthracene units within layers form dihedral angles of 13.2 (1)°. C—H⋯O interactions from the piperidine rings to the C=O group of the amide are observed between layers.

Related literature

For further information regarding CP-640186, see: Harwood et al. (2003 ); Zhang et al. (2004 ).

Experimental

Crystal data

C₂₀H₁₉NO
M_r = 289.36
Monoclinic, C 2/c
a = 26.393 (5) Å
b = 7.3950 (15) Å
c = 18.213 (4) Å
β = 120.29 (3)°
V = 3069.5 (14) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 (2) K
0.30 × 0.10 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.977, T_max = 0.992
2828 measured reflections
2762 independent reflections
1678 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.081
wR(F²) = 0.278
S = 1.09
2762 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17B⋯O1ⁱ	0.97	2.41	3.342 (5)	162
C20—H20A⋯O1ⁱⁱ	0.97	2.71	3.557 (5)	146
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y, -z+1.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808033205/bi2300sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808033205/bi2300Isup2.hkl

checkCIF report

Comment top

Inhibition of acetyl-CoA carboxylase (ACC), with its resultant inhibition of fatty acid synthesis and stimulation of fatty acid oxidation, has the potential to affect favourably the multitude of cardiovascular risk factors associated with the metabolic syndrome. Recent findings reported by Pfizer researchers show that the isozyme-nonselective ACC inhibitor CP-640186 inhibits both the lipogenic tissue isozyme (ACC1) and the oxidative tissue isozyme (ACC2) (Harwood et al., 2003). The title compound is a sub-structure of CP-640186 (see Zhang et al., 2004).

Related literature top

For further information regarding CP-640186, see: Harwood et al. (2003); Zhang et al. (2004).

Experimental top

A mixture of 9-carbonyl anthracene (1 mmol) and piperidine (1.2 mmol) with 1.5 mmol DCC (DCC = N,N'-dicyclohexyl-carbodiimide) was stirred in 5 ml CH₂Cl₂ at room temperature for 1 h to yield the title compound. Crystals were obtained from acetone/petroleum ether.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound with displacement ellipsoids shown at 30% probability for non-H atoms.

(Anthracen-9-yl)(piperidin-1-yl)methanone top

Crystal data top

C₂₀H₁₉NO	F(000) = 1232
M_r = 289.36	D_x = 1.252 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 781 reflections
a = 26.393 (5) Å	θ = 2.4–28.0°
b = 7.3950 (15) Å	µ = 0.08 mm⁻¹
c = 18.213 (4) Å	T = 293 K
β = 120.29 (3)°	Block, yellow
V = 3069.5 (14) Å³	0.30 × 0.10 × 0.10 mm
Z = 8

Data collection top

Bruker SMART APEX CCD diffractometer	2762 independent reflections
Radiation source: fine-focus sealed tube	1678 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ϕ and ω scans	θ_max = 25.2°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −31→27
T_min = 0.977, T_max = 0.992	k = 0→8
2828 measured reflections	l = 0→21

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)] = 0.081	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.278	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.1523P)² + 2.2222P] where P = (F_o² + 2F_c²)/3
2762 reflections	(Δ/σ)_max < 0.001
199 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₂₀H₁₉NO	V = 3069.5 (14) Å³
M_r = 289.36	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 26.393 (5) Å	µ = 0.08 mm⁻¹
b = 7.3950 (15) Å	T = 293 K
c = 18.213 (4) Å	0.30 × 0.10 × 0.10 mm
β = 120.29 (3)°

Data collection top

Bruker SMART APEX CCD diffractometer	2762 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	1678 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.992	R_int = 0.025
2828 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.081	0 restraints
wR(F²) = 0.278	H-atom parameters constrained
S = 1.09	Δρ_max = 0.32 e Å⁻³
2762 reflections	Δρ_min = −0.29 e Å⁻³
199 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
C1	0.83354 (17)	0.1537 (5)	0.6866 (3)	0.0733 (11)
H1A	0.8709	0.1589	0.6936	0.088*
C2	0.78453 (17)	0.1309 (5)	0.6048 (3)	0.0680 (10)
H2A	0.7896	0.1254	0.5579	0.082*
C3	0.72989 (15)	0.1169 (5)	0.5938 (2)	0.0577 (9)
H3A	0.6980	0.0993	0.5394	0.069*
C4	0.72079 (13)	0.1286 (4)	0.66384 (19)	0.0472 (8)
C5	0.77079 (14)	0.1544 (4)	0.7464 (2)	0.0504 (8)
C6	0.82684 (15)	0.1679 (5)	0.7541 (2)	0.0611 (9)
H6A	0.8596	0.1871	0.8074	0.073*
C7	0.66500 (13)	0.1159 (4)	0.65502 (19)	0.0480 (8)
C8	0.65705 (14)	0.1315 (4)	0.7257 (2)	0.0478 (8)
C9	0.70746 (15)	0.1503 (4)	0.8081 (2)	0.0534 (8)
C10	0.76293 (14)	0.1644 (4)	0.8162 (2)	0.0538 (9)
H10A	0.7956	0.1809	0.8699	0.065*
C11	0.60162 (16)	0.1229 (5)	0.7191 (3)	0.0626 (10)
H11A	0.5682	0.1098	0.6658	0.075*
C12	0.59630 (19)	0.1335 (5)	0.7889 (3)	0.0751 (12)
H12A	0.5591	0.1308	0.7826	0.090*
C13	0.6455 (2)	0.1485 (5)	0.8706 (3)	0.0718 (11)
H13A	0.6409	0.1535	0.9180	0.086*
C14	0.69916 (19)	0.1556 (5)	0.8799 (2)	0.0677 (10)
H14A	0.7317	0.1642	0.9343	0.081*
C15	0.61267 (14)	0.0678 (5)	0.5689 (2)	0.0524 (8)
C16	0.59033 (17)	0.3956 (5)	0.5392 (2)	0.0693 (11)
H16A	0.6271	0.4108	0.5922	0.083*
H16B	0.5593	0.4463	0.5465	0.083*
C17	0.5933 (2)	0.4948 (6)	0.4705 (3)	0.0870 (13)
H17A	0.6274	0.4549	0.4680	0.104*
H17B	0.5975	0.6232	0.4831	0.104*
C18	0.5372 (2)	0.4617 (6)	0.3833 (3)	0.0848 (13)
H18A	0.5036	0.5164	0.3828	0.102*
H18B	0.5416	0.5166	0.3384	0.102*
C19	0.52736 (19)	0.2577 (7)	0.3679 (2)	0.0861 (13)
H19A	0.4905	0.2372	0.3156	0.103*
H19B	0.5585	0.2072	0.3607	0.103*
C20	0.52607 (17)	0.1630 (6)	0.4382 (2)	0.0798 (12)
H20A	0.4917	0.2008	0.4406	0.096*
H20B	0.5233	0.0337	0.4281	0.096*
N1	0.57930 (13)	0.2033 (4)	0.51987 (17)	0.0652 (9)
O1	0.60244 (11)	−0.0901 (3)	0.54889 (16)	0.0754 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.058 (2)	0.078 (3)	0.090 (3)	0.0004 (18)	0.042 (2)	0.008 (2)
C2	0.076 (3)	0.071 (2)	0.071 (2)	0.0052 (19)	0.048 (2)	0.0061 (19)
C3	0.059 (2)	0.063 (2)	0.0532 (19)	0.0000 (16)	0.0293 (17)	0.0003 (15)
C4	0.0487 (18)	0.0408 (16)	0.0483 (18)	0.0024 (13)	0.0216 (15)	0.0022 (13)
C5	0.0448 (17)	0.0440 (17)	0.0513 (18)	0.0004 (13)	0.0160 (15)	0.0049 (14)
C6	0.0438 (19)	0.060 (2)	0.068 (2)	0.0006 (15)	0.0189 (17)	−0.0010 (17)
C7	0.0475 (18)	0.0449 (18)	0.0438 (17)	0.0006 (13)	0.0173 (14)	0.0000 (13)
C8	0.0527 (19)	0.0420 (17)	0.0519 (18)	−0.0014 (13)	0.0286 (16)	0.0008 (13)
C9	0.059 (2)	0.0469 (18)	0.0481 (18)	0.0035 (15)	0.0229 (16)	−0.0049 (14)
C10	0.0507 (19)	0.0506 (19)	0.0459 (18)	0.0015 (14)	0.0139 (15)	0.0006 (14)
C11	0.059 (2)	0.062 (2)	0.071 (2)	−0.0058 (16)	0.0350 (19)	−0.0031 (17)
C12	0.078 (3)	0.077 (3)	0.093 (3)	−0.001 (2)	0.060 (3)	−0.002 (2)
C13	0.099 (3)	0.070 (2)	0.068 (2)	0.011 (2)	0.058 (2)	0.0023 (19)
C14	0.084 (3)	0.068 (2)	0.054 (2)	−0.0005 (19)	0.036 (2)	−0.0040 (17)
C15	0.0497 (18)	0.057 (2)	0.0485 (18)	−0.0007 (15)	0.0238 (15)	−0.0044 (16)
C16	0.070 (2)	0.066 (2)	0.057 (2)	0.0051 (18)	0.0207 (19)	−0.0063 (18)
C17	0.112 (4)	0.063 (3)	0.085 (3)	0.003 (2)	0.049 (3)	0.003 (2)
C18	0.110 (3)	0.076 (3)	0.064 (2)	0.013 (2)	0.040 (2)	0.016 (2)
C19	0.086 (3)	0.103 (4)	0.050 (2)	−0.007 (2)	0.020 (2)	−0.003 (2)
C20	0.060 (2)	0.092 (3)	0.058 (2)	−0.012 (2)	0.0075 (19)	0.003 (2)
N1	0.0575 (18)	0.0608 (19)	0.0531 (17)	−0.0090 (14)	0.0100 (14)	0.0008 (14)
O1	0.0812 (19)	0.0499 (15)	0.0646 (16)	−0.0093 (12)	0.0144 (14)	−0.0150 (12)

Geometric parameters (Å, º) top

C1—C6	1.333 (5)	C12—H12A	0.930
C1—C2	1.406 (5)	C13—C14	1.339 (6)
C1—H1A	0.930	C13—H13A	0.930
C2—C3	1.356 (5)	C14—H14A	0.930
C2—H2A	0.930	C15—O1	1.213 (4)
C3—C4	1.415 (4)	C15—N1	1.336 (4)
C3—H3A	0.930	C16—N1	1.458 (5)
C4—C7	1.401 (4)	C16—C17	1.486 (6)
C4—C5	1.427 (4)	C16—H16A	0.970
C5—C10	1.389 (5)	C16—H16B	0.970
C5—C6	1.417 (5)	C17—C18	1.549 (6)
C6—H6A	0.930	C17—H17A	0.970
C7—C8	1.409 (4)	C17—H17B	0.970
C7—C15	1.519 (4)	C18—C19	1.532 (6)
C8—C11	1.407 (5)	C18—H18A	0.970
C8—C9	1.424 (5)	C18—H18B	0.970
C9—C10	1.399 (5)	C19—C20	1.476 (6)
C9—C14	1.433 (5)	C19—H19A	0.970
C10—H10A	0.930	C19—H19B	0.970
C11—C12	1.351 (5)	C20—N1	1.472 (4)
C11—H11A	0.930	C20—H20A	0.970
C12—C13	1.401 (6)	C20—H20B	0.970

C6—C1—C2	120.5 (3)	C13—C14—C9	121.5 (4)
C6—C1—H1A	119.7	C13—C14—H14A	119.3
C2—C1—H1A	119.7	C9—C14—H14A	119.3
C3—C2—C1	120.5 (4)	O1—C15—N1	123.3 (3)
C3—C2—H2A	119.8	O1—C15—C7	119.0 (3)
C1—C2—H2A	119.8	N1—C15—C7	117.7 (3)
C2—C3—C4	120.9 (3)	N1—C16—C17	111.5 (3)
C2—C3—H3A	119.5	N1—C16—H16A	109.3
C4—C3—H3A	119.5	C17—C16—H16A	109.3
C7—C4—C3	122.6 (3)	N1—C16—H16B	109.3
C7—C4—C5	119.3 (3)	C17—C16—H16B	109.3
C3—C4—C5	118.1 (3)	H16A—C16—H16B	108.0
C10—C5—C6	122.4 (3)	C16—C17—C18	110.9 (4)
C10—C5—C4	119.0 (3)	C16—C17—H17A	109.5
C6—C5—C4	118.6 (3)	C18—C17—H17A	109.5
C1—C6—C5	121.4 (3)	C16—C17—H17B	109.5
C1—C6—H6A	119.3	C18—C17—H17B	109.5
C5—C6—H6A	119.3	H17A—C17—H17B	108.0
C4—C7—C8	121.4 (3)	C19—C18—C17	109.2 (3)
C4—C7—C15	119.3 (3)	C19—C18—H18A	109.8
C8—C7—C15	119.0 (3)	C17—C18—H18A	109.8
C11—C8—C7	123.0 (3)	C19—C18—H18B	109.8
C11—C8—C9	118.2 (3)	C17—C18—H18B	109.8
C7—C8—C9	118.7 (3)	H18A—C18—H18B	108.3
C10—C9—C8	119.4 (3)	C20—C19—C18	112.6 (4)
C10—C9—C14	122.4 (3)	C20—C19—H19A	109.1
C8—C9—C14	118.2 (3)	C18—C19—H19A	109.1
C5—C10—C9	122.0 (3)	C20—C19—H19B	109.1
C5—C10—H10A	119.0	C18—C19—H19B	109.1
C9—C10—H10A	119.0	H19A—C19—H19B	107.8
C12—C11—C8	120.9 (4)	N1—C20—C19	110.7 (3)
C12—C11—H11A	119.5	N1—C20—H20A	109.5
C8—C11—H11A	119.5	C19—C20—H20A	109.5
C11—C12—C13	121.6 (4)	N1—C20—H20B	109.5
C11—C12—H12A	119.2	C19—C20—H20B	109.5
C13—C12—H12A	119.2	H20A—C20—H20B	108.1
C14—C13—C12	119.5 (4)	C15—N1—C16	125.9 (3)
C14—C13—H13A	120.3	C15—N1—C20	119.7 (3)
C12—C13—H13A	120.3	C16—N1—C20	114.4 (3)

C6—C1—C2—C3	−2.2 (6)	C8—C9—C10—C5	−2.3 (5)
C1—C2—C3—C4	1.3 (5)	C14—C9—C10—C5	178.3 (3)
C2—C3—C4—C7	179.6 (3)	C7—C8—C11—C12	178.1 (3)
C2—C3—C4—C5	−0.4 (5)	C9—C8—C11—C12	0.5 (5)
C7—C4—C5—C10	0.7 (4)	C8—C11—C12—C13	−1.7 (6)
C3—C4—C5—C10	−179.3 (3)	C11—C12—C13—C14	1.1 (6)
C7—C4—C5—C6	−179.7 (3)	C12—C13—C14—C9	0.7 (6)
C3—C4—C5—C6	0.3 (4)	C10—C9—C14—C13	177.5 (3)
C2—C1—C6—C5	2.2 (6)	C8—C9—C14—C13	−1.9 (5)
C10—C5—C6—C1	178.4 (3)	C4—C7—C15—O1	84.2 (4)
C4—C5—C6—C1	−1.2 (5)	C8—C7—C15—O1	−90.4 (4)
C3—C4—C7—C8	−178.8 (3)	C4—C7—C15—N1	−97.4 (4)
C5—C4—C7—C8	1.2 (4)	C8—C7—C15—N1	88.0 (4)
C3—C4—C7—C15	6.7 (5)	N1—C16—C17—C18	54.6 (5)
C5—C4—C7—C15	−173.3 (3)	C16—C17—C18—C19	−53.5 (5)
C4—C7—C8—C11	178.8 (3)	C17—C18—C19—C20	53.9 (5)
C15—C7—C8—C11	−6.7 (5)	C18—C19—C20—N1	−54.1 (5)
C4—C7—C8—C9	−3.6 (4)	O1—C15—N1—C16	−177.9 (4)
C15—C7—C8—C9	170.9 (3)	C7—C15—N1—C16	3.7 (5)
C11—C8—C9—C10	−178.2 (3)	O1—C15—N1—C20	2.1 (5)
C7—C8—C9—C10	4.1 (4)	C7—C15—N1—C20	−176.3 (3)
C11—C8—C9—C14	1.3 (4)	C17—C16—N1—C15	124.0 (4)
C7—C8—C9—C14	−176.5 (3)	C17—C16—N1—C20	−56.0 (5)
C6—C5—C10—C9	−179.8 (3)	C19—C20—N1—C15	−125.0 (4)
C4—C5—C10—C9	−0.1 (5)	C19—C20—N1—C16	55.1 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17B···O1ⁱ	0.97	2.41	3.342 (5)	162
C20—H20A···O1ⁱⁱ	0.97	2.71	3.557 (5)	146

Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₉NO
M_r	289.36
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	26.393 (5), 7.3950 (15), 18.213 (4)
β (°)	120.29 (3)
V (Å³)	3069.5 (14)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.977, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	2828, 2762, 1678
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.081, 0.278, 1.09
No. of reflections	2762
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.29

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SAINT (Bruker, 2000, SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17B···O1ⁱ	0.97	2.41	3.342 (5)	162.0
C20—H20A···O1ⁱⁱ	0.97	2.71	3.557 (5)	145.7

Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y, −z+1.

Acknowledgements

The authors acknowledge financial support from the Natural Science Foundation of Jiangsu Province (grant No. BK2007132).

References

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