1-(Piperidin-1-yl)-9,10-anthraquinone.

In the title compound, C(19)H(17)NO(2), the piperidine ring adopts a chair conformation. The mean planes of the piperidine ring and the anthracene ring system are inclined at a dihedral angle of 38.7 (1)°. In the crystal, adjacent mol-ecules are linked through C-H⋯π and π-π [centroid-centroid distance = 3.782 (1) Å] inter-actions, forming a layer parallel to the bc plane.

Related literature

For general background to and applications of anthraquinone derivatives, see: Alves et al. (2004 ▶); Czupryniak et al. (2012 ▶); Wang et al. (2011 ▶); Yeh & Wang (2006 ▶). For related structures, see: Niedziałkowski et al. (2011 ▶); Yatsenko et al. (2000 ▶).

Experimental

Crystal data

C19H17NO2

M = 291.34

Monoclinic,

a = 16.7798 (4) Å

b = 6.84599 (14) Å

c = 12.6126 (3) Å

β = 90.723 (2)°

V = 1448.75 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.42 × 0.35 × 0.05 mm

Data collection

Oxford Diffraction GEMINI R ULTRA Ruby CCD diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.969, T max = 0.996

18914 measured reflections

2565 independent reflections

2189 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.106

S = 1.04

2565 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2008 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812037713/is5185sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812037713/is5185Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812037713/is5185Isup3.cml

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

C19H17NO2	F(000) = 616
Mr = 291.34	Dx = 1.336 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 10180 reflections
a = 16.7798 (4) Å	θ = 3.4–29.3°
b = 6.84599 (14) Å	µ = 0.09 mm−1
c = 12.6126 (3) Å	T = 295 K
β = 90.723 (2)°	Plate, red
V = 1448.75 (6) Å3	0.42 × 0.35 × 0.05 mm
Z = 4

Oxford Diffraction GEMINI R ULTRA Ruby CCD diffractometer	2565 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2189 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 10.4002 pixels mm-1	θmax = 25.1°, θmin = 3.4°
ω scans	h = −20→20
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −8→8
Tmin = 0.969, Tmax = 0.996	l = −15→15
18914 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0585P)2 + 0.233P] where P = (Fo2 + 2Fc2)/3
2565 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 0.12 e Å−3
0 restraints	Δρmin = −0.21 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.

	x	y	z	Uiso*/Ueq
C1	0.25956 (7)	0.80184 (16)	0.58372 (9)	0.0352 (3)
C2	0.31025 (8)	0.95054 (19)	0.62053 (11)	0.0451 (3)
H2	0.2900	1.0455	0.6655	0.054*
C3	0.38886 (9)	0.9603 (2)	0.59230 (12)	0.0530 (4)
H3	0.4212	1.0592	0.6195	0.064*
C4	0.42001 (8)	0.82494 (19)	0.52427 (11)	0.0473 (3)
H4	0.4729	0.8347	0.5036	0.057*
C5	0.40087 (8)	0.22450 (19)	0.31080 (10)	0.0454 (3)
H5	0.4535	0.2399	0.2900	0.054*
C6	0.35703 (9)	0.0683 (2)	0.27434 (11)	0.0532 (4)
H6	0.3799	−0.0223	0.2290	0.064*
C7	0.27893 (10)	0.0461 (2)	0.30517 (12)	0.0574 (4)
H7	0.2488	−0.0573	0.2785	0.069*
C8	0.24507 (9)	0.17570 (18)	0.37514 (11)	0.0476 (3)
H8	0.1928	0.1572	0.3968	0.057*
C9	0.25025 (7)	0.47080 (18)	0.48949 (10)	0.0397 (3)
C10	0.41166 (7)	0.53500 (18)	0.41201 (10)	0.0405 (3)
C11	0.29271 (7)	0.65477 (17)	0.51749 (9)	0.0344 (3)
C12	0.37301 (7)	0.67421 (17)	0.48642 (9)	0.0369 (3)
C13	0.28871 (7)	0.33387 (17)	0.41345 (9)	0.0370 (3)
C14	0.36646 (7)	0.35977 (17)	0.37891 (9)	0.0371 (3)
N15	0.18002 (6)	0.80008 (15)	0.61441 (8)	0.0378 (3)
C16	0.11888 (7)	0.8051 (2)	0.53068 (10)	0.0455 (3)
H16A	0.1361	0.7265	0.4712	0.055*
H16B	0.1119	0.9383	0.5061	0.055*
C17	0.04046 (8)	0.7281 (2)	0.57052 (12)	0.0547 (4)
H17A	0.0463	0.5918	0.5901	0.066*
H17B	0.0004	0.7369	0.5146	0.066*
C18	0.01381 (8)	0.8450 (2)	0.66587 (12)	0.0561 (4)
H18A	0.0013	0.9777	0.6444	0.067*
H18B	−0.0339	0.7871	0.6950	0.067*
C19	0.07945 (8)	0.8471 (2)	0.74937 (11)	0.0516 (4)
H19A	0.0638	0.9307	0.8076	0.062*
H19B	0.0869	0.7161	0.7770	0.062*
C20	0.15707 (8)	0.91992 (19)	0.70485 (10)	0.0452 (3)
H20A	0.1512	1.0549	0.6826	0.054*
H20B	0.1984	0.9142	0.7592	0.054*
O21	0.18687 (6)	0.42388 (15)	0.52784 (10)	0.0682 (3)
O22	0.47785 (6)	0.56781 (15)	0.37776 (9)	0.0607 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0364 (6)	0.0372 (6)	0.0320 (6)	−0.0020 (5)	−0.0002 (5)	0.0035 (5)
C2	0.0474 (8)	0.0424 (7)	0.0457 (7)	−0.0052 (5)	0.0029 (6)	−0.0085 (6)
C3	0.0491 (8)	0.0500 (8)	0.0600 (9)	−0.0166 (6)	0.0019 (7)	−0.0124 (7)
C4	0.0375 (7)	0.0500 (8)	0.0546 (8)	−0.0115 (5)	0.0059 (6)	−0.0026 (6)
C5	0.0478 (7)	0.0490 (7)	0.0395 (7)	0.0071 (6)	0.0057 (6)	0.0011 (6)
C6	0.0666 (10)	0.0464 (8)	0.0468 (8)	0.0066 (7)	0.0065 (7)	−0.0079 (6)
C7	0.0716 (10)	0.0429 (8)	0.0577 (9)	−0.0096 (7)	0.0036 (8)	−0.0115 (6)
C8	0.0500 (8)	0.0424 (7)	0.0505 (8)	−0.0081 (6)	0.0053 (6)	−0.0017 (6)
C9	0.0374 (7)	0.0398 (7)	0.0420 (7)	−0.0059 (5)	0.0066 (5)	−0.0001 (5)
C10	0.0382 (7)	0.0450 (7)	0.0386 (6)	−0.0029 (5)	0.0053 (5)	0.0048 (5)
C11	0.0359 (6)	0.0355 (6)	0.0319 (6)	−0.0035 (5)	0.0009 (5)	0.0027 (5)
C12	0.0365 (6)	0.0380 (6)	0.0363 (6)	−0.0043 (5)	0.0030 (5)	0.0041 (5)
C13	0.0422 (7)	0.0338 (6)	0.0350 (6)	−0.0018 (5)	0.0019 (5)	0.0040 (5)
C14	0.0408 (7)	0.0385 (6)	0.0319 (6)	0.0010 (5)	0.0017 (5)	0.0045 (5)
N15	0.0361 (6)	0.0443 (6)	0.0331 (5)	0.0007 (4)	0.0007 (4)	−0.0050 (4)
C16	0.0405 (7)	0.0576 (8)	0.0384 (7)	−0.0002 (6)	−0.0027 (5)	−0.0008 (6)
C17	0.0401 (7)	0.0658 (9)	0.0583 (9)	−0.0045 (6)	−0.0018 (6)	−0.0042 (7)
C18	0.0413 (8)	0.0607 (9)	0.0667 (10)	0.0037 (6)	0.0112 (7)	0.0017 (7)
C19	0.0535 (8)	0.0564 (8)	0.0452 (8)	0.0071 (6)	0.0129 (6)	−0.0030 (6)
C20	0.0480 (7)	0.0464 (7)	0.0414 (7)	0.0033 (6)	0.0025 (6)	−0.0084 (6)
O21	0.0557 (6)	0.0568 (6)	0.0930 (8)	−0.0234 (5)	0.0358 (6)	−0.0244 (6)
O22	0.0451 (6)	0.0679 (7)	0.0696 (7)	−0.0129 (5)	0.0234 (5)	−0.0109 (5)

C1—N15	1.3943 (15)	C10—O22	1.2176 (15)
C1—C2	1.4020 (17)	C10—C14	1.4766 (17)
C1—C11	1.4257 (17)	C10—C12	1.4917 (18)
C2—C3	1.3722 (19)	C11—C12	1.4142 (17)
C2—H2	0.9300	C13—C14	1.3919 (17)
C3—C4	1.3707 (19)	N15—C20	1.4608 (15)
C3—H3	0.9300	N15—C16	1.4634 (16)
C4—C12	1.3804 (17)	C16—C17	1.5094 (19)
C4—H4	0.9300	C16—H16A	0.9700
C5—C6	1.374 (2)	C16—H16B	0.9700
C5—C14	1.3934 (18)	C17—C18	1.517 (2)
C5—H5	0.9300	C17—H17A	0.9700
C6—C7	1.380 (2)	C17—H17B	0.9700
C6—H6	0.9300	C18—C19	1.514 (2)
C7—C8	1.379 (2)	C18—H18A	0.9700
C7—H7	0.9300	C18—H18B	0.9700
C8—C13	1.3905 (18)	C19—C20	1.5094 (19)
C8—H8	0.9300	C19—H19A	0.9700
C9—O21	1.2171 (15)	C19—H19B	0.9700
C9—C11	1.4873 (17)	C20—H20A	0.9700
C9—C13	1.4936 (17)	C20—H20B	0.9700
N15—C1—C2	119.55 (11)	C14—C13—C9	122.36 (11)
N15—C1—C11	122.58 (10)	C13—C14—C5	120.37 (12)
C2—C1—C11	117.86 (11)	C13—C14—C10	119.68 (11)
C3—C2—C1	122.03 (12)	C5—C14—C10	119.92 (11)
C3—C2—H2	119.0	C1—N15—C20	118.34 (10)
C1—C2—H2	119.0	C1—N15—C16	117.66 (9)
C4—C3—C2	120.34 (12)	C20—N15—C16	111.16 (10)
C4—C3—H3	119.8	N15—C16—C17	110.97 (11)
C2—C3—H3	119.8	N15—C16—H16A	109.4
C3—C4—C12	120.06 (12)	C17—C16—H16A	109.4
C3—C4—H4	120.0	N15—C16—H16B	109.4
C12—C4—H4	120.0	C17—C16—H16B	109.4
C6—C5—C14	119.96 (13)	H16A—C16—H16B	108.0
C6—C5—H5	120.0	C16—C17—C18	110.29 (12)
C14—C5—H5	120.0	C16—C17—H17A	109.6
C5—C6—C7	119.84 (12)	C18—C17—H17A	109.6
C5—C6—H6	120.1	C16—C17—H17B	109.6
C7—C6—H6	120.1	C18—C17—H17B	109.6
C8—C7—C6	120.67 (13)	H17A—C17—H17B	108.1
C8—C7—H7	119.7	C19—C18—C17	109.72 (11)
C6—C7—H7	119.7	C19—C18—H18A	109.7
C7—C8—C13	120.26 (13)	C17—C18—H18A	109.7
C7—C8—H8	119.9	C19—C18—H18B	109.7
C13—C8—H8	119.9	C17—C18—H18B	109.7
O21—C9—C11	123.20 (11)	H18A—C18—H18B	108.2
O21—C9—C13	118.45 (11)	C20—C19—C18	111.59 (11)
C11—C9—C13	118.32 (10)	C20—C19—H19A	109.3
O22—C10—C14	121.14 (12)	C18—C19—H19A	109.3
O22—C10—C12	120.74 (11)	C20—C19—H19B	109.3
C14—C10—C12	118.10 (10)	C18—C19—H19B	109.3
C12—C11—C1	118.43 (10)	H19A—C19—H19B	108.0
C12—C11—C9	117.97 (10)	N15—C20—C19	110.02 (11)
C1—C11—C9	123.22 (11)	N15—C20—H20A	109.7
C4—C12—C11	121.11 (11)	C19—C20—H20A	109.7
C4—C12—C10	116.37 (11)	N15—C20—H20B	109.7
C11—C12—C10	122.52 (11)	C19—C20—H20B	109.7
C8—C13—C14	118.82 (11)	H20A—C20—H20B	108.2
C8—C13—C9	118.81 (11)
N15—C1—C2—C3	−179.53 (12)	O21—C9—C13—C8	11.05 (19)
C11—C1—C2—C3	1.84 (19)	C11—C9—C13—C8	−171.04 (11)
C1—C2—C3—C4	1.5 (2)	O21—C9—C13—C14	−169.48 (12)
C2—C3—C4—C12	−2.1 (2)	C11—C9—C13—C14	8.43 (17)
C14—C5—C6—C7	0.1 (2)	C8—C13—C14—C5	−2.79 (18)
C5—C6—C7—C8	−2.2 (2)	C9—C13—C14—C5	177.74 (11)
C6—C7—C8—C13	1.7 (2)	C8—C13—C14—C10	175.23 (11)
N15—C1—C11—C12	176.97 (10)	C9—C13—C14—C10	−4.24 (17)
C2—C1—C11—C12	−4.45 (16)	C6—C5—C14—C13	2.36 (18)
N15—C1—C11—C9	−10.26 (17)	C6—C5—C14—C10	−175.66 (12)
C2—C1—C11—C9	168.32 (11)	O22—C10—C14—C13	−175.33 (12)
O21—C9—C11—C12	166.47 (13)	C12—C10—C14—C13	2.97 (17)
C13—C9—C11—C12	−11.33 (16)	O22—C10—C14—C5	2.71 (18)
O21—C9—C11—C1	−6.3 (2)	C12—C10—C14—C5	−179.00 (10)
C13—C9—C11—C1	175.87 (10)	C2—C1—N15—C20	−16.08 (16)
C3—C4—C12—C11	−0.7 (2)	C11—C1—N15—C20	162.48 (11)
C3—C4—C12—C10	179.43 (12)	C2—C1—N15—C16	122.15 (12)
C1—C11—C12—C4	3.98 (17)	C11—C1—N15—C16	−59.30 (15)
C9—C11—C12—C4	−169.18 (11)	C1—N15—C16—C17	158.76 (11)
C1—C11—C12—C10	−176.15 (10)	C20—N15—C16—C17	−60.21 (14)
C9—C11—C12—C10	10.69 (17)	N15—C16—C17—C18	57.32 (16)
O22—C10—C12—C4	−8.32 (18)	C16—C17—C18—C19	−54.05 (16)
C14—C10—C12—C4	173.38 (11)	C17—C18—C19—C20	54.41 (16)
O22—C10—C12—C11	171.81 (12)	C1—N15—C20—C19	−159.99 (11)
C14—C10—C12—C11	−6.49 (17)	C16—N15—C20—C19	59.26 (13)
C7—C8—C13—C14	0.77 (19)	C18—C19—C20—N15	−56.84 (15)
C7—C8—C13—C9	−179.74 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cg3i	0.93	2.88	3.685 (2)	146

I	J	CgI···CgJ	Dihedral angle	CgI_Perp	CgJ_Perp	CgI_Offset	CgJ_Offset
2	3ii	3.782 (1)	3.31 (6)	3.615 (1)	3.660 (1)	1.112 (1)	0.953 (1)

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C5–C8/C13/C14 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯Cg3i	0.93	2.88	3.685 (2)	146

Symmetry code: (i) .