1-Dimethyl-amino-9,10-anthraquinone.

In the crystal structure of the title compound, C(16)H(13)NO(2), adjacent mol-ecules are linked through C-H⋯π and π-π [centroid-centroid distances = 3.844 (2) Å] contacts. The anthracene ring system and dimethyl-amino group are oriented at a dihedral angle of 38.4 (1)°. In the crystal, the mean planes of adjacent anthracene units are inclined at angles of 59.3 (1), 75.7 (1) and 76.0 (1)°.

Related literature

For general background to anthraquinones, see: Arai et al. (1985 ▶); Dalliya et al. (2007 ▶); Gatto et al. (1996 ▶); Kowalczyk et al. (2010 ▶); Mori et al. (1990 ▶); Ossowski et al. (2005 ▶); Zoń et al. (2003 ▶). For a related structure, see: Yatsenko et al. (2000 ▶). For mol­ecular inter­actions, see: Hunter et al. (2001 ▶); Spek (2009 ▶); Takahashi et al. (2001 ▶).

Experimental

Crystal data

C16H13NO2

M = 251.27

Orthorhombic,

a = 7.2823 (3) Å

b = 11.1519 (7) Å

c = 14.9834 (7) Å

V = 1216.82 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.45 × 0.20 × 0.18 mm

Data collection

Oxford Diffraction Gemini R ULTRA Ruby CCD diffractometer

4683 measured reflections

1258 independent reflections

918 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.079

S = 0.96

1258 reflections

174 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.18 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, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811006829/ng5119sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811006829/ng5119Isup2.hkl

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

C16H13NO2	F(000) = 528
Mr = 251.27	Dx = 1.372 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1944 reflections
a = 7.2823 (3) Å	θ = 3.1–29.0°
b = 11.1519 (7) Å	µ = 0.09 mm−1
c = 14.9834 (7) Å	T = 295 K
V = 1216.82 (11) Å3	Prism, red
Z = 4	0.45 × 0.20 × 0.18 mm

Oxford Diffraction Gemini R ULTRA Ruby CCD diffractometer	918 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray Source	Rint = 0.033
graphite	θmax = 25.1°, θmin = 3.1°
Detector resolution: 10.4002 pixels mm-1	h = −8→6
ω scans	k = −12→13
4683 measured reflections	l = −17→13
1258 independent 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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079	H-atom parameters constrained
S = 0.96	w = 1/[σ2(Fo2) + (0.0492P)2] where P = (Fo2 + 2Fc2)/3
1258 reflections	(Δ/σ)max < 0.001
174 parameters	Δρmax = 0.12 e Å−3
0 restraints	Δρmin = −0.18 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	0.7457 (3)	0.5675 (2)	0.53415 (14)	0.0349 (6)
C2	0.8768 (3)	0.6609 (3)	0.53396 (17)	0.0437 (7)
H2	0.9738	0.6578	0.4937	0.052*
C3	0.8647 (4)	0.7554 (3)	0.59116 (18)	0.0486 (7)
H3	0.9530	0.8155	0.5892	0.058*
C4	0.7235 (3)	0.7630 (2)	0.65179 (17)	0.0422 (6)
H4	0.7206	0.8255	0.6928	0.051*
C5	0.1522 (4)	0.6067 (3)	0.78267 (16)	0.0459 (7)
H5	0.1608	0.6622	0.8288	0.055*
C6	0.0081 (4)	0.5277 (3)	0.78088 (18)	0.0487 (7)
H6	−0.0795	0.5290	0.8260	0.058*
C7	−0.0067 (3)	0.4466 (3)	0.71212 (17)	0.0465 (7)
H7	−0.1065	0.3946	0.7099	0.056*
C8	0.1262 (3)	0.4422 (2)	0.64640 (17)	0.0409 (6)
H8	0.1164	0.3863	0.6006	0.049*
C9	0.4157 (3)	0.5148 (2)	0.57716 (15)	0.0334 (6)
C10	0.4341 (4)	0.6937 (2)	0.71603 (16)	0.0394 (7)
C11	0.5878 (3)	0.5814 (2)	0.58994 (14)	0.0325 (6)
C12	0.5869 (3)	0.6781 (2)	0.65160 (16)	0.0335 (6)
C13	0.2744 (3)	0.5206 (2)	0.64829 (15)	0.0335 (6)
C14	0.2856 (3)	0.6048 (2)	0.71661 (14)	0.0354 (6)
N15	0.7757 (3)	0.4671 (2)	0.48311 (13)	0.0421 (6)
C16	0.7173 (4)	0.3491 (2)	0.51109 (19)	0.0528 (8)
H16A	0.6745	0.3525	0.5716	0.079*
H16B	0.8189	0.2945	0.5072	0.079*
H16C	0.6198	0.3219	0.4730	0.079*
C17	0.9195 (3)	0.4667 (3)	0.41526 (17)	0.0552 (8)
H17A	0.9068	0.5362	0.3780	0.083*
H17B	0.9086	0.3957	0.3794	0.083*
H17C	1.0376	0.4679	0.4437	0.083*
O18	0.3823 (2)	0.45881 (18)	0.50827 (11)	0.0484 (5)
O19	0.4317 (3)	0.77920 (19)	0.76763 (15)	0.0644 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0328 (13)	0.0405 (16)	0.0315 (12)	0.0014 (14)	−0.0002 (12)	0.0029 (12)
C2	0.0356 (14)	0.0555 (19)	0.0400 (14)	−0.0071 (15)	0.0045 (12)	0.0082 (14)
C3	0.0453 (14)	0.0471 (17)	0.0532 (16)	−0.0149 (15)	−0.0037 (15)	0.0040 (17)
C4	0.0427 (14)	0.0392 (16)	0.0448 (14)	−0.0052 (14)	−0.0053 (13)	−0.0071 (14)
C5	0.0478 (15)	0.0464 (18)	0.0435 (14)	0.0079 (15)	0.0064 (13)	−0.0049 (14)
C6	0.0377 (14)	0.057 (2)	0.0512 (15)	0.0046 (16)	0.0143 (12)	0.0078 (17)
C7	0.0345 (14)	0.0513 (19)	0.0538 (16)	−0.0061 (14)	−0.0005 (13)	0.0095 (17)
C8	0.0348 (13)	0.0461 (16)	0.0416 (13)	−0.0012 (13)	−0.0033 (12)	0.0038 (14)
C9	0.0339 (12)	0.0348 (15)	0.0314 (12)	0.0014 (12)	−0.0027 (11)	0.0011 (12)
C10	0.0434 (15)	0.0391 (16)	0.0358 (14)	0.0024 (13)	−0.0017 (13)	−0.0039 (13)
C11	0.0296 (12)	0.0372 (15)	0.0306 (12)	0.0010 (12)	−0.0026 (11)	0.0048 (12)
C12	0.0317 (12)	0.0346 (14)	0.0342 (12)	0.0011 (13)	−0.0051 (12)	0.0036 (12)
C13	0.0284 (12)	0.0364 (15)	0.0358 (12)	0.0050 (12)	−0.0062 (11)	0.0035 (12)
C14	0.0319 (13)	0.0378 (15)	0.0364 (12)	0.0035 (12)	−0.0001 (12)	0.0014 (13)
N15	0.0347 (11)	0.0497 (14)	0.0418 (11)	−0.0001 (12)	0.0084 (10)	−0.0042 (12)
C16	0.0510 (16)	0.0460 (18)	0.0614 (17)	0.0072 (16)	0.0043 (15)	−0.0056 (16)
C17	0.0407 (14)	0.076 (2)	0.0489 (15)	0.0057 (17)	0.0081 (13)	−0.0116 (16)
O18	0.0404 (10)	0.0629 (12)	0.0418 (10)	−0.0084 (10)	0.0001 (8)	−0.0145 (10)
O19	0.0661 (13)	0.0604 (14)	0.0665 (13)	−0.0108 (11)	0.0160 (11)	−0.0280 (13)

C1—N15	1.373 (3)	C8—H8	0.9300
C1—C2	1.413 (4)	C9—O18	1.230 (3)
C1—C11	1.430 (3)	C9—C11	1.469 (3)
C2—C3	1.360 (4)	C9—C13	1.483 (3)
C2—H2	0.9300	C10—O19	1.227 (3)
C3—C4	1.374 (4)	C10—C14	1.467 (4)
C3—H3	0.9300	C10—C12	1.483 (3)
C4—C12	1.374 (3)	C11—C12	1.420 (3)
C4—H4	0.9300	C13—C14	1.392 (3)
C5—C6	1.370 (4)	N15—C16	1.446 (3)
C5—C14	1.387 (3)	N15—C17	1.459 (3)
C5—H5	0.9300	C16—H16A	0.9600
C6—C7	1.375 (4)	C16—H16B	0.9600
C6—H6	0.9300	C16—H16C	0.9600
C7—C8	1.382 (3)	C17—H17A	0.9600
C7—H7	0.9300	C17—H17B	0.9600
C8—C13	1.389 (3)	C17—H17C	0.9600
N15—C1—C2	119.5 (2)	C14—C10—C12	118.5 (2)
N15—C1—C11	122.8 (2)	C12—C11—C1	117.8 (2)
C2—C1—C11	117.7 (2)	C12—C11—C9	117.7 (2)
C3—C2—C1	121.7 (2)	C1—C11—C9	123.7 (2)
C3—C2—H2	119.1	C4—C12—C11	121.4 (2)
C1—C2—H2	119.1	C4—C12—C10	117.5 (2)
C2—C3—C4	120.8 (3)	C11—C12—C10	121.1 (2)
C2—C3—H3	119.6	C8—C13—C14	119.0 (2)
C4—C3—H3	119.6	C8—C13—C9	119.8 (2)
C12—C4—C3	119.9 (2)	C14—C13—C9	121.1 (2)
C12—C4—H4	120.1	C5—C14—C13	119.6 (2)
C3—C4—H4	120.1	C5—C14—C10	120.7 (2)
C6—C5—C14	120.9 (2)	C13—C14—C10	119.7 (2)
C6—C5—H5	119.6	C1—N15—C16	122.26 (19)
C14—C5—H5	119.6	C1—N15—C17	120.3 (2)
C5—C6—C7	119.8 (2)	C16—N15—C17	114.2 (2)
C5—C6—H6	120.1	N15—C16—H16A	109.5
C7—C6—H6	120.1	N15—C16—H16B	109.5
C6—C7—C8	120.2 (2)	H16A—C16—H16B	109.5
C6—C7—H7	119.9	N15—C16—H16C	109.5
C8—C7—H7	119.9	H16A—C16—H16C	109.5
C7—C8—C13	120.5 (2)	H16B—C16—H16C	109.5
C7—C8—H8	119.8	N15—C17—H17A	109.5
C13—C8—H8	119.8	N15—C17—H17B	109.5
O18—C9—C11	122.3 (2)	H17A—C17—H17B	109.5
O18—C9—C13	119.2 (2)	N15—C17—H17C	109.5
C11—C9—C13	118.4 (2)	H17A—C17—H17C	109.5
O19—C10—C14	120.7 (2)	H17B—C17—H17C	109.5
O19—C10—C12	120.8 (2)
N15—C1—C2—C3	−172.0 (2)	O19—C10—C12—C11	−178.1 (2)
C11—C1—C2—C3	6.6 (3)	C14—C10—C12—C11	1.8 (3)
C1—C2—C3—C4	0.2 (4)	C7—C8—C13—C14	−0.9 (3)
C2—C3—C4—C12	−3.7 (4)	C7—C8—C13—C9	−179.9 (2)
C14—C5—C6—C7	−1.0 (4)	O18—C9—C13—C8	14.8 (3)
C5—C6—C7—C8	1.9 (4)	C11—C9—C13—C8	−168.1 (2)
C6—C7—C8—C13	−1.0 (4)	O18—C9—C13—C14	−164.1 (2)
N15—C1—C11—C12	168.8 (2)	C11—C9—C13—C14	12.9 (3)
C2—C1—C11—C12	−9.8 (3)	C6—C5—C14—C13	−0.9 (4)
N15—C1—C11—C9	−21.7 (3)	C6—C5—C14—C10	176.6 (2)
C2—C1—C11—C9	159.7 (2)	C8—C13—C14—C5	1.9 (3)
O18—C9—C11—C12	155.6 (2)	C9—C13—C14—C5	−179.2 (2)
C13—C9—C11—C12	−21.3 (3)	C8—C13—C14—C10	−175.7 (2)
O18—C9—C11—C1	−13.8 (4)	C9—C13—C14—C10	3.3 (3)
C13—C9—C11—C1	169.2 (2)	O19—C10—C14—C5	−8.3 (4)
C3—C4—C12—C11	0.2 (4)	C12—C10—C14—C5	171.8 (2)
C3—C4—C12—C10	−177.5 (2)	O19—C10—C14—C13	169.2 (2)
C1—C11—C12—C4	6.6 (3)	C12—C10—C14—C13	−10.7 (3)
C9—C11—C12—C4	−163.5 (2)	C2—C1—N15—C16	145.7 (2)
C1—C11—C12—C10	−175.8 (2)	C11—C1—N15—C16	−32.9 (3)
C9—C11—C12—C10	14.1 (3)	C2—C1—N15—C17	−12.9 (3)
O19—C10—C12—C4	−0.4 (4)	C11—C1—N15—C17	168.5 (2)
C14—C10—C12—C4	179.5 (2)

Cg1 and Cg2 are the centroids of the C1–C4/C11/C12 and C5–C8/C13/C14 rings respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cg1i	0.93	2.99	3.724 (3)	137
C4—H4···Cg2ii	0.93	2.81	3.678 (3)	156

I	J	CgI···CgJ	Dihedral angle	CgI_Perp	CgI_Offset
1	2iii	3.844 (2)	11.13 (12)	3.606 (10)	1.334 (10)
2	1iv	3.844 (2)	11.13 (12)	3.606 (10)	1.334 (10)

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C4/C11/C12 and C5–C8/C13/C14 rings respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯Cg1i	0.93	2.99	3.724 (3)	137
C4—H4⋯Cg2ii	0.93	2.81	3.678 (3)	156

Symmetry codes: (i) ; (ii) .