2-(Dimethyl­amino)­anthraquinone

Abstract

The mol­ecule of the title compound, C₁₆H₁₃NO₂, is almost planar, with a maximum deviation of 0.013 (2) Å from the best plane; the dihedral angle between the two aromatic rings is 1.06 (1)°. In the crystal, mol­ecules are linked through weak intra­molecular C—H⋯O inter­actions, forming chains running parallel to [10].

Related literature

For the preparation, see: Havlik et al. (2008 ▶). For a related structure, see: Janczak (1995 ▶).

Experimental

Crystal data

• C₁₆H₁₃NO₂

• M _r = 251.27

• Monoclinic,

• a = 4.8614 (6) Å

• b = 19.945 (2) Å

• c = 12.8624 (15) Å

• β = 95.979 (2)°

• V = 1240.3 (3) ų

• Z = 4

• Mo Kα radiation

• μ = 0.09 mm⁻¹

• T = 298 K

• 0.23 × 0.20 × 0.12 mm

Data collection

• Bruker SMART CCD area-detector diffractometer

• 14833 measured reflections

• 3050 independent reflections

• 2267 reflections with I > 2σ(I)

• R _int = 0.022

Refinement

• R[F ² > 2σ(F ²)] = 0.055

• wR(F ²) = 0.161

• S = 1.03

• 3050 reflections

• 174 parameters

• H-atom parameters constrained

• Δρ_max = 0.30 e Å⁻³

• Δρ_min = −0.17 e Å⁻³

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1999 ▶); 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.

Supplementary Material

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O1i	0.93	2.50	3.272 (2)	140

Symmetry code: (i) .

supplementary crystallographic information

Comment

The aminoanthraquinone derivatives are important compounds as dyes and intermediates. We report here the crystal structure of the title compound.

The molecular is almost planar, with a maximum deviation of 0.013 (2)Å from the best plane. The dihedral angle between the two benzene rings is 1.06 (1)° (Fig 1). The bond distances and bond angles are in good agreement with those in a closely related crystal structure (Janczak et al., 1995). In the crystal structure, the crystal packing is stabilized by a weak intramolecular C(9)—H(9)···O(1) (x + 1/2, -y + 1/2, z - 1/2) hydrogen bond [C(9)···O(1) 3.275 (2) Å1,Table 1].

Experimental

The title compound was synthesized according to the reported literature (Havlik et al., 2008). Crystals of (I) suitablefor X-ray diffraction were grown by slow evaporation of a chloroform-methanol(1:1) solution of the title compound under 293 K.

Refinement

All H atoms were positioned in geometrically idealized positions and constrained to ride on their parent atoms, with C—H distances in the range 0.93–0.98 Å and U_iso(H) = 1.2U_eq(C) or U_iso(H) = 1.5U_eq(C).

Figures

Fig. 1.

A view of (I), showing the atom-labelling scheme, with displacement ellipsoids drawn at the 30% probability level. H atoms omitted for clarity.

Crystal data

C16H13NO2	F(000) = 528
Mr = 251.27	Dx = 1.346 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4567 reflections
a = 4.8614 (6) Å	θ = 2.6–28.1°
b = 19.945 (2) Å	µ = 0.09 mm−1
c = 12.8624 (15) Å	T = 298 K
β = 95.979 (2)°	Block, red
V = 1240.3 (3) Å3	0.23 × 0.20 × 0.12 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	2267 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.022
graphite	θmax = 28.3°, θmin = 2.6°
phi and ω scans	h = −6→6
14833 measured reflections	k = −26→26
3050 independent reflections	l = −17→17

Refinement

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0842P)2 + 0.2178P] where P = (Fo2 + 2Fc2)/3
3050 reflections	(Δ/σ)max < 0.001
174 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.6324 (3)	−0.00602 (7)	0.25988 (10)	0.0429 (3)
C2	0.6624 (3)	0.00659 (8)	0.36860 (11)	0.0478 (3)
H2	0.5603	−0.0184	0.4120	0.057*
C3	0.8390 (3)	0.05496 (8)	0.41090 (10)	0.0478 (4)
H3	0.8533	0.0623	0.4827	0.057*
C4	0.9988 (3)	0.09367 (7)	0.34945 (10)	0.0426 (3)
C5	1.1903 (3)	0.14348 (8)	0.39853 (11)	0.0505 (4)
C6	1.3534 (3)	0.18380 (7)	0.32916 (12)	0.0473 (3)
C7	1.5374 (4)	0.23222 (9)	0.37330 (14)	0.0618 (4)
H7	1.5556	0.2395	0.4451	0.074*
C8	1.6923 (4)	0.26926 (9)	0.30989 (17)	0.0708 (5)
H8	1.8159	0.3012	0.3395	0.085*
C9	1.6661 (4)	0.25959 (9)	0.20389 (17)	0.0677 (5)
H9	1.7712	0.2850	0.1621	0.081*
C10	1.4840 (3)	0.21210 (8)	0.15899 (14)	0.0580 (4)
H10	1.4665	0.2057	0.0870	0.070*
C11	1.3265 (3)	0.17382 (7)	0.22145 (11)	0.0461 (3)
C12	1.1329 (3)	0.12237 (8)	0.17157 (11)	0.0471 (3)
C13	0.9685 (3)	0.08246 (7)	0.24153 (10)	0.0407 (3)
C14	0.7881 (3)	0.03404 (7)	0.19746 (10)	0.0438 (3)
H14	0.7694	0.0279	0.1254	0.053*
C15	0.3016 (4)	−0.09571 (9)	0.28401 (14)	0.0622 (4)
H15A	0.4210	−0.1127	0.3422	0.093*
H15B	0.2182	−0.1325	0.2443	0.093*
H15C	0.1597	−0.0685	0.3092	0.093*
C16	0.3996 (4)	−0.06205 (9)	0.10626 (13)	0.0647 (5)
H16A	0.3266	−0.0204	0.0778	0.097*
H16B	0.2655	−0.0970	0.0911	0.097*
H16C	0.5656	−0.0730	0.0755	0.097*
N1	0.4616 (3)	−0.05562 (7)	0.21809 (10)	0.0534 (3)
O1	1.2204 (3)	0.15165 (7)	0.49310 (9)	0.0779 (4)
O2	1.1100 (3)	0.11368 (7)	0.07767 (8)	0.0725 (4)

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
C1	0.0394 (7)	0.0500 (7)	0.0395 (7)	0.0056 (6)	0.0045 (5)	0.0006 (6)
C2	0.0503 (8)	0.0574 (8)	0.0372 (7)	−0.0002 (6)	0.0118 (6)	0.0048 (6)
C3	0.0533 (8)	0.0607 (9)	0.0300 (6)	0.0038 (6)	0.0072 (5)	−0.0004 (6)
C4	0.0428 (7)	0.0500 (8)	0.0348 (7)	0.0063 (6)	0.0031 (5)	0.0003 (5)
C5	0.0528 (8)	0.0572 (8)	0.0405 (7)	0.0033 (7)	0.0007 (6)	−0.0029 (6)
C6	0.0428 (7)	0.0468 (7)	0.0511 (8)	0.0049 (6)	−0.0008 (6)	0.0015 (6)
C7	0.0619 (10)	0.0573 (9)	0.0636 (10)	−0.0020 (8)	−0.0054 (8)	−0.0038 (8)
C8	0.0616 (11)	0.0525 (9)	0.0953 (15)	−0.0101 (8)	−0.0066 (9)	0.0051 (9)
C9	0.0583 (10)	0.0566 (10)	0.0880 (14)	−0.0053 (8)	0.0064 (9)	0.0207 (9)
C10	0.0536 (9)	0.0602 (9)	0.0604 (10)	0.0034 (7)	0.0073 (7)	0.0147 (7)
C11	0.0403 (7)	0.0492 (8)	0.0486 (8)	0.0069 (6)	0.0037 (6)	0.0068 (6)
C12	0.0456 (8)	0.0590 (8)	0.0371 (7)	0.0037 (6)	0.0060 (6)	0.0040 (6)
C13	0.0389 (7)	0.0486 (7)	0.0347 (6)	0.0064 (5)	0.0043 (5)	0.0024 (5)
C14	0.0456 (7)	0.0558 (8)	0.0301 (6)	0.0039 (6)	0.0043 (5)	0.0002 (6)
C15	0.0617 (10)	0.0640 (10)	0.0616 (10)	−0.0096 (8)	0.0105 (8)	0.0028 (8)
C16	0.0747 (11)	0.0685 (10)	0.0499 (9)	−0.0116 (9)	0.0008 (8)	−0.0073 (8)
N1	0.0556 (7)	0.0605 (8)	0.0445 (7)	−0.0093 (6)	0.0065 (5)	−0.0016 (6)
O1	0.0973 (10)	0.0948 (10)	0.0405 (6)	−0.0258 (8)	0.0023 (6)	−0.0124 (6)
O2	0.0806 (8)	0.1016 (10)	0.0368 (6)	−0.0258 (7)	0.0128 (5)	−0.0003 (6)

Geometric parameters (Å, °)

C1—N1	1.3651 (19)	C9—C10	1.381 (3)
C1—C14	1.4079 (19)	C9—H9	0.9300
C1—C2	1.4133 (19)	C10—C11	1.394 (2)
C2—C3	1.366 (2)	C10—H10	0.9300
C2—H2	0.9300	C11—C12	1.491 (2)
C3—C4	1.3970 (19)	C12—O2	1.2138 (17)
C3—H3	0.9300	C12—C13	1.4939 (19)
C4—C13	1.3987 (18)	C13—C14	1.385 (2)
C4—C5	1.459 (2)	C14—H14	0.9300
C5—O1	1.2208 (17)	C15—N1	1.449 (2)
C5—C6	1.490 (2)	C15—H15A	0.9600
C6—C11	1.392 (2)	C15—H15B	0.9600
C6—C7	1.396 (2)	C15—H15C	0.9600
C7—C8	1.380 (3)	C16—N1	1.444 (2)
C7—H7	0.9300	C16—H16A	0.9600
C8—C9	1.370 (3)	C16—H16B	0.9600
C8—H8	0.9300	C16—H16C	0.9600
N1—C1—C14	121.85 (12)	C11—C10—H10	120.0
N1—C1—C2	120.95 (13)	C6—C11—C10	119.66 (14)
C14—C1—C2	117.20 (13)	C6—C11—C12	121.08 (13)
C3—C2—C1	121.02 (13)	C10—C11—C12	119.26 (14)
C3—C2—H2	119.5	O2—C12—C11	120.97 (13)
C1—C2—H2	119.5	O2—C12—C13	121.60 (14)
C2—C3—C4	121.89 (12)	C11—C12—C13	117.43 (12)
C2—C3—H3	119.1	C14—C13—C4	120.94 (12)
C4—C3—H3	119.1	C14—C13—C12	118.73 (12)
C3—C4—C13	117.77 (13)	C4—C13—C12	120.33 (13)
C3—C4—C5	119.92 (12)	C13—C14—C1	121.15 (12)
C13—C4—C5	122.31 (13)	C13—C14—H14	119.4
O1—C5—C4	121.78 (14)	C1—C14—H14	119.4
O1—C5—C6	120.58 (14)	N1—C15—H15A	109.5
C4—C5—C6	117.64 (12)	N1—C15—H15B	109.5
C11—C6—C7	119.56 (14)	H15A—C15—H15B	109.5
C11—C6—C5	121.20 (13)	N1—C15—H15C	109.5
C7—C6—C5	119.23 (14)	H15A—C15—H15C	109.5
C8—C7—C6	119.71 (17)	H15B—C15—H15C	109.5
C8—C7—H7	120.1	N1—C16—H16A	109.5
C6—C7—H7	120.1	N1—C16—H16B	109.5
C9—C8—C7	120.86 (17)	H16A—C16—H16B	109.5
C9—C8—H8	119.6	N1—C16—H16C	109.5
C7—C8—H8	119.6	H16A—C16—H16C	109.5
C8—C9—C10	120.12 (16)	H16B—C16—H16C	109.5
C8—C9—H9	119.9	C1—N1—C16	120.78 (13)
C10—C9—H9	119.9	C1—N1—C15	120.72 (12)
C9—C10—C11	120.08 (17)	C16—N1—C15	117.68 (13)
C9—C10—H10	120.0
N1—C1—C2—C3	178.16 (13)	C9—C10—C11—C6	0.1 (2)
C14—C1—C2—C3	−1.1 (2)	C9—C10—C11—C12	−179.45 (14)
C1—C2—C3—C4	−0.5 (2)	C6—C11—C12—O2	−179.89 (14)
C2—C3—C4—C13	1.3 (2)	C10—C11—C12—O2	−0.4 (2)
C2—C3—C4—C5	−178.30 (14)	C6—C11—C12—C13	0.4 (2)
C3—C4—C5—O1	1.6 (2)	C10—C11—C12—C13	179.92 (13)
C13—C4—C5—O1	−178.05 (14)	C3—C4—C13—C14	−0.7 (2)
C3—C4—C5—C6	−179.42 (12)	C5—C4—C13—C14	178.97 (13)
C13—C4—C5—C6	1.0 (2)	C3—C4—C13—C12	179.82 (12)
O1—C5—C6—C11	178.32 (15)	C5—C4—C13—C12	−0.5 (2)
C4—C5—C6—C11	−0.7 (2)	O2—C12—C13—C14	0.6 (2)
O1—C5—C6—C7	−1.4 (2)	C11—C12—C13—C14	−179.66 (12)
C4—C5—C6—C7	179.60 (13)	O2—C12—C13—C4	−179.87 (14)
C11—C6—C7—C8	−0.5 (2)	C11—C12—C13—C4	−0.14 (19)
C5—C6—C7—C8	179.16 (15)	C4—C13—C14—C1	−0.9 (2)
C6—C7—C8—C9	0.6 (3)	C12—C13—C14—C1	178.63 (12)
C7—C8—C9—C10	−0.3 (3)	N1—C1—C14—C13	−177.49 (13)
C8—C9—C10—C11	−0.1 (3)	C2—C1—C14—C13	1.7 (2)
C7—C6—C11—C10	0.2 (2)	C14—C1—N1—C16	−10.0 (2)
C5—C6—C11—C10	−179.49 (13)	C2—C1—N1—C16	170.79 (14)
C7—C6—C11—C12	179.74 (13)	C14—C1—N1—C15	−179.41 (14)
C5—C6—C11—C12	0.0 (2)	C2—C1—N1—C15	1.4 (2)

Hydrogen-bond geometry (Å, °)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1i	0.93	2.50	3.272 (2)	140

Symmetry codes: (i) x+1/2, −y+1/2, z−1/2.