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

The title compound, C(20)H(19)NO, is a substructure of CP-640186, a potent inhibitor of mammalian acetyl-coenzyme A carboxyl-ases. 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. Mol-ecules are arranged into layers parallel to (100) and adjacent anthracene units within layers form dihedral angles of 13.2 (1)°. C-H⋯O inter-actions 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 = 289.36

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.081

wR(F 2) = 0.278

S = 1.09

2762 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.29 e Å−3

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.

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

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

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

C20H19NO	F(000) = 1232
Mr = 289.36	Dx = 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

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

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(Fo2) + (0.1523P)2 + 2.2222P] where P = (Fo2 + 2Fc2)/3
2762 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) ; (ii) .