1,5-Bis(piperidin-1-yl)-9,10-anthraquin-one.

In the centrosymmetric title compound, C24H26N2O2, the piperidine ring adopts a chair conformation and is inclined at a dihedral angle of 37.5 (1)°to the anthracene ring system. In the crystal, adjacent mol-ecules are linked through C-H⋯π and π-π [centroid-centroid distances = 3.806 (1) Å] inter-actions, forming a layer parallel to the bc plane.

Related literature

For general background to quinone compounds, see: Alves et al. (2004 ▶); El-Najjar et al. (2011 ▶); Czupryniak et al. (2012 ▶); Krohn (2008 ▶); Wannalerse et al. (2008 ▶). For related structures, see: Niedziałkowski et al. (2010 ▶, 2011 ▶); Wnuk et al. (2012 ▶); Yatsenko et al. (2000 ▶).

Experimental

Crystal data

C24H26N2O2

M = 374.47

Monoclinic,

a = 10.9115 (4) Å

b = 7.0127 (2) Å

c = 12.5984 (5) Å

β = 97.819 (4)°

V = 955.05 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 295 K

0.45 × 0.22 × 0.05 mm

Data collection

Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.909, T max = 1.000

12625 measured reflections

1699 independent reflections

1274 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.102

S = 1.04

1699 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.14 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812050313/xu5662sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812050313/xu5662Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812050313/xu5662Isup3.cml

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

C24H26N2O2	F(000) = 400
Mr = 374.47	Dx = 1.302 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5096 reflections
a = 10.9115 (4) Å	θ = 3.3–29.2°
b = 7.0127 (2) Å	µ = 0.08 mm−1
c = 12.5984 (5) Å	T = 295 K
β = 97.819 (4)°	Plate, dark-red
V = 955.05 (6) Å3	0.45 × 0.22 × 0.05 mm
Z = 2

Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer	1699 independent reflections
Radiation source: Enhanced (Mo) X-ray Source	1274 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
Detector resolution: 10.4002 pixels mm-1	θmax = 25.1°, θmin = 3.3°
ω scans	h = −13→13
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −8→8
Tmin = 0.909, Tmax = 1.000	l = −15→15
12625 measured reflections

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0491P)2 + 0.0697P] where P = (Fo2 + 2Fc2)/3
1699 reflections	(Δ/σ)max < 0.001
127 parameters	Δρmax = 0.13 e Å−3
0 restraints	Δρmin = −0.14 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

	x	y	z	Uiso*/Ueq
C1	0.09986 (14)	0.19940 (19)	0.37606 (11)	0.0393 (4)
C2	0.01598 (16)	0.0605 (2)	0.33222 (14)	0.0513 (4)
H2	0.0428	−0.0338	0.2889	0.062*
C3	−0.10447 (16)	0.0595 (2)	0.35124 (15)	0.0559 (5)
H3	−0.1586	−0.0320	0.3184	0.067*
C4	−0.14652 (15)	0.1917 (2)	0.41814 (13)	0.0472 (4)
H4	−0.2273	0.1852	0.4338	0.057*
C5	−0.06790 (13)	0.33481 (18)	0.46218 (12)	0.0383 (4)
C6	0.05433 (13)	0.34603 (18)	0.43854 (11)	0.0368 (4)
C7	0.12218 (14)	0.5249 (2)	0.46817 (13)	0.0430 (4)
O8	0.21900 (12)	0.56569 (16)	0.43513 (12)	0.0720 (4)
N9	0.22226 (11)	0.19390 (17)	0.35623 (10)	0.0436 (3)
C10	0.32009 (14)	0.1930 (2)	0.44808 (12)	0.0499 (4)
H10A	0.3308	0.0645	0.4763	0.060*
H10B	0.2961	0.2742	0.5041	0.060*
C11	0.44077 (15)	0.2628 (3)	0.41651 (14)	0.0588 (5)
H11A	0.5047	0.2570	0.4780	0.071*
H11B	0.4320	0.3946	0.3934	0.071*
C12	0.47827 (16)	0.1425 (3)	0.32700 (15)	0.0609 (5)
H12A	0.4974	0.0141	0.3527	0.073*
H12B	0.5518	0.1958	0.3030	0.073*
C13	0.37392 (16)	0.1369 (3)	0.23460 (14)	0.0578 (5)
H13A	0.3628	0.2630	0.2032	0.069*
H13B	0.3958	0.0507	0.1800	0.069*
C14	0.25403 (16)	0.0721 (2)	0.27005 (14)	0.0537 (5)
H14A	0.1884	0.0772	0.2099	0.064*
H14B	0.2621	−0.0588	0.2948	0.064*

	U11	U22	U33	U12	U13	U23
C1	0.0474 (9)	0.0385 (8)	0.0304 (8)	−0.0024 (6)	−0.0002 (7)	0.0035 (6)
C2	0.0595 (11)	0.0423 (9)	0.0505 (11)	−0.0062 (8)	0.0019 (9)	−0.0084 (7)
C3	0.0566 (11)	0.0439 (9)	0.0651 (12)	−0.0167 (8)	0.0002 (9)	−0.0133 (8)
C4	0.0447 (9)	0.0413 (8)	0.0546 (10)	−0.0110 (7)	0.0028 (8)	−0.0001 (7)
C5	0.0438 (9)	0.0341 (7)	0.0354 (8)	−0.0056 (6)	−0.0009 (7)	0.0058 (6)
C6	0.0425 (9)	0.0349 (7)	0.0313 (8)	−0.0050 (6)	−0.0012 (7)	0.0029 (6)
C7	0.0424 (9)	0.0419 (8)	0.0444 (10)	−0.0089 (7)	0.0049 (8)	0.0008 (7)
O8	0.0637 (8)	0.0614 (8)	0.0985 (11)	−0.0251 (6)	0.0386 (8)	−0.0237 (7)
N9	0.0458 (8)	0.0498 (7)	0.0340 (7)	0.0008 (6)	0.0010 (6)	−0.0046 (6)
C10	0.0501 (10)	0.0603 (10)	0.0375 (10)	−0.0003 (7)	−0.0009 (8)	0.0037 (8)
C11	0.0489 (11)	0.0720 (11)	0.0539 (11)	−0.0041 (8)	0.0018 (9)	0.0006 (9)
C12	0.0520 (11)	0.0673 (11)	0.0640 (13)	0.0094 (8)	0.0101 (9)	0.0045 (9)
C13	0.0668 (12)	0.0613 (10)	0.0478 (11)	0.0120 (9)	0.0162 (9)	−0.0037 (9)
C14	0.0614 (11)	0.0528 (9)	0.0457 (11)	0.0040 (8)	0.0032 (9)	−0.0116 (8)

C1—N9	1.3923 (19)	N9—C10	1.4637 (19)
C1—C2	1.398 (2)	C10—C11	1.508 (2)
C1—C6	1.425 (2)	C10—H10A	0.9700
C2—C3	1.368 (2)	C10—H10B	0.9700
C2—H2	0.9300	C11—C12	1.509 (2)
C3—C4	1.373 (2)	C11—H11A	0.9700
C3—H3	0.9300	C11—H11B	0.9700
C4—C5	1.386 (2)	C12—C13	1.514 (2)
C4—H4	0.9300	C12—H12A	0.9700
C5—C6	1.4078 (19)	C12—H12B	0.9700
C5—C7i	1.493 (2)	C13—C14	1.509 (2)
C6—C7	1.479 (2)	C13—H13A	0.9700
C7—O8	1.2209 (18)	C13—H13B	0.9700
C7—C5i	1.493 (2)	C14—H14A	0.9700
N9—C14	1.4595 (19)	C14—H14B	0.9700
N9—C1—C2	120.15 (13)	N9—C10—H10B	109.4
N9—C1—C6	122.30 (13)	C11—C10—H10B	109.4
C2—C1—C6	117.53 (14)	H10A—C10—H10B	108.0
C3—C2—C1	121.86 (15)	C10—C11—C12	110.53 (15)
C3—C2—H2	119.1	C10—C11—H11A	109.5
C1—C2—H2	119.1	C12—C11—H11A	109.5
C2—C3—C4	120.87 (14)	C10—C11—H11B	109.5
C2—C3—H3	119.6	C12—C11—H11B	109.5
C4—C3—H3	119.6	H11A—C11—H11B	108.1
C3—C4—C5	119.62 (15)	C11—C12—C13	109.70 (14)
C3—C4—H4	120.2	C11—C12—H12A	109.7
C5—C4—H4	120.2	C13—C12—H12A	109.7
C4—C5—C6	120.55 (14)	C11—C12—H12B	109.7
C4—C5—C7i	116.03 (14)	C13—C12—H12B	109.7
C6—C5—C7i	123.40 (12)	H12A—C12—H12B	108.2
C5—C6—C1	119.22 (12)	C14—C13—C12	111.83 (15)
C5—C6—C7	116.76 (13)	C14—C13—H13A	109.3
C1—C6—C7	123.47 (13)	C12—C13—H13A	109.3
O8—C7—C6	122.64 (14)	C14—C13—H13B	109.3
O8—C7—C5i	118.49 (13)	C12—C13—H13B	109.3
C6—C7—C5i	118.83 (13)	H13A—C13—H13B	107.9
C1—N9—C14	118.71 (12)	N9—C14—C13	110.33 (13)
C1—N9—C10	118.19 (12)	N9—C14—H14A	109.6
C14—N9—C10	111.35 (12)	C13—C14—H14A	109.6
N9—C10—C11	111.04 (13)	N9—C14—H14B	109.6
N9—C10—H10A	109.4	C13—C14—H14B	109.6
C11—C10—H10A	109.4	H14A—C14—H14B	108.1
N9—C1—C2—C3	178.97 (15)	C1—C6—C7—O8	5.0 (2)
C6—C1—C2—C3	−2.4 (2)	C5—C6—C7—C5i	11.1 (2)
C1—C2—C3—C4	−2.6 (3)	C1—C6—C7—C5i	−177.48 (13)
C2—C3—C4—C5	3.7 (3)	C2—C1—N9—C14	14.6 (2)
C3—C4—C5—C6	0.2 (2)	C6—C1—N9—C14	−163.92 (13)
C3—C4—C5—C7i	178.57 (15)	C2—C1—N9—C10	−125.26 (15)
C4—C5—C6—C1	−5.3 (2)	C6—C1—N9—C10	56.21 (18)
C7i—C5—C6—C1	176.55 (13)	C1—N9—C10—C11	−157.87 (14)
C4—C5—C6—C7	166.56 (14)	C14—N9—C10—C11	59.50 (17)
C7i—C5—C6—C7	−11.6 (2)	N9—C10—C11—C12	−57.34 (18)
N9—C1—C6—C5	−175.20 (13)	C10—C11—C12—C13	54.17 (19)
C2—C1—C6—C5	6.2 (2)	C11—C12—C13—C14	−54.10 (19)
N9—C1—C6—C7	13.6 (2)	C1—N9—C14—C13	159.33 (13)
C2—C1—C6—C7	−164.99 (14)	C10—N9—C14—C13	−58.25 (17)
C5—C6—C7—O8	−166.46 (16)	C12—C13—C14—N9	56.03 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cg2ii	0.93	2.98	3.850 (2)	156

I	J	CgI···CgJ	Dihedral angle	CgI_Perp	CgJ_Perp	CgI_Offset	CgJ_Offset
2	2ii	3.806 (1)	0	3.702 (1)	3.702 (1)	0.884 (1)	0.884 (1)

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯Cg2i	0.93	2.98	3.850 (2)	156

Symmetry code: (i) .