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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): o3091.
Published online 2010 November 6. doi:  10.1107/S1600536810044636
PMCID: PMC3011451

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 [10An external file that holds a picture, illustration, etc.
Object name is e-66-o3091-efi1.jpg].

Related literature

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

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Object name is e-66-o3091-scheme1.jpg

Experimental

Crystal data

  • C16H13NO2
  • M r = 251.27
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o3091-efi2.jpg
  • a = 4.8614 (6) Å
  • b = 19.945 (2) Å
  • c = 12.8624 (15) Å
  • β = 95.979 (2)°
  • V = 1240.3 (3) Å3
  • 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
  • Δρmax = 0.30 e Å−3
  • Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1999 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810044636/ng5045sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810044636/ng5045Isup2.hkl

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

Acknowledgments

The author are grateful to Central China Normal University for financial support and thank Dr Xiang-Gao Meng for the data collection.

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 Uiso(H) = 1.2Ueq(C) or Uiso(H) = 1.5Ueq(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

C16H13NO2F(000) = 528
Mr = 251.27Dx = 1.346 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4567 reflections
a = 4.8614 (6) Åθ = 2.6–28.1°
b = 19.945 (2) ŵ = 0.09 mm1
c = 12.8624 (15) ÅT = 298 K
β = 95.979 (2)°Block, red
V = 1240.3 (3) Å30.23 × 0.20 × 0.12 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer2267 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.022
graphiteθmax = 28.3°, θmin = 2.6°
phi and ω scansh = −6→6
14833 measured reflectionsk = −26→26
3050 independent reflectionsl = −17→17

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0842P)2 + 0.2178P] where P = (Fo2 + 2Fc2)/3
3050 reflections(Δ/σ)max < 0.001
174 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = −0.17 e Å3

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 (Å2)

xyzUiso*/Ueq
C10.6324 (3)−0.00602 (7)0.25988 (10)0.0429 (3)
C20.6624 (3)0.00659 (8)0.36860 (11)0.0478 (3)
H20.5603−0.01840.41200.057*
C30.8390 (3)0.05496 (8)0.41090 (10)0.0478 (4)
H30.85330.06230.48270.057*
C40.9988 (3)0.09367 (7)0.34945 (10)0.0426 (3)
C51.1903 (3)0.14348 (8)0.39853 (11)0.0505 (4)
C61.3534 (3)0.18380 (7)0.32916 (12)0.0473 (3)
C71.5374 (4)0.23222 (9)0.37330 (14)0.0618 (4)
H71.55560.23950.44510.074*
C81.6923 (4)0.26926 (9)0.30989 (17)0.0708 (5)
H81.81590.30120.33950.085*
C91.6661 (4)0.25959 (9)0.20389 (17)0.0677 (5)
H91.77120.28500.16210.081*
C101.4840 (3)0.21210 (8)0.15899 (14)0.0580 (4)
H101.46650.20570.08700.070*
C111.3265 (3)0.17382 (7)0.22145 (11)0.0461 (3)
C121.1329 (3)0.12237 (8)0.17157 (11)0.0471 (3)
C130.9685 (3)0.08246 (7)0.24153 (10)0.0407 (3)
C140.7881 (3)0.03404 (7)0.19746 (10)0.0438 (3)
H140.76940.02790.12540.053*
C150.3016 (4)−0.09571 (9)0.28401 (14)0.0622 (4)
H15A0.4210−0.11270.34220.093*
H15B0.2182−0.13250.24430.093*
H15C0.1597−0.06850.30920.093*
C160.3996 (4)−0.06205 (9)0.10626 (13)0.0647 (5)
H16A0.3266−0.02040.07780.097*
H16B0.2655−0.09700.09110.097*
H16C0.5656−0.07300.07550.097*
N10.4616 (3)−0.05562 (7)0.21809 (10)0.0534 (3)
O11.2204 (3)0.15165 (7)0.49310 (9)0.0779 (4)
O21.1100 (3)0.11368 (7)0.07767 (8)0.0725 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0394 (7)0.0500 (7)0.0395 (7)0.0056 (6)0.0045 (5)0.0006 (6)
C20.0503 (8)0.0574 (8)0.0372 (7)−0.0002 (6)0.0118 (6)0.0048 (6)
C30.0533 (8)0.0607 (9)0.0300 (6)0.0038 (6)0.0072 (5)−0.0004 (6)
C40.0428 (7)0.0500 (8)0.0348 (7)0.0063 (6)0.0031 (5)0.0003 (5)
C50.0528 (8)0.0572 (8)0.0405 (7)0.0033 (7)0.0007 (6)−0.0029 (6)
C60.0428 (7)0.0468 (7)0.0511 (8)0.0049 (6)−0.0008 (6)0.0015 (6)
C70.0619 (10)0.0573 (9)0.0636 (10)−0.0020 (8)−0.0054 (8)−0.0038 (8)
C80.0616 (11)0.0525 (9)0.0953 (15)−0.0101 (8)−0.0066 (9)0.0051 (9)
C90.0583 (10)0.0566 (10)0.0880 (14)−0.0053 (8)0.0064 (9)0.0207 (9)
C100.0536 (9)0.0602 (9)0.0604 (10)0.0034 (7)0.0073 (7)0.0147 (7)
C110.0403 (7)0.0492 (8)0.0486 (8)0.0069 (6)0.0037 (6)0.0068 (6)
C120.0456 (8)0.0590 (8)0.0371 (7)0.0037 (6)0.0060 (6)0.0040 (6)
C130.0389 (7)0.0486 (7)0.0347 (6)0.0064 (5)0.0043 (5)0.0024 (5)
C140.0456 (7)0.0558 (8)0.0301 (6)0.0039 (6)0.0043 (5)0.0002 (6)
C150.0617 (10)0.0640 (10)0.0616 (10)−0.0096 (8)0.0105 (8)0.0028 (8)
C160.0747 (11)0.0685 (10)0.0499 (9)−0.0116 (9)0.0008 (8)−0.0073 (8)
N10.0556 (7)0.0605 (8)0.0445 (7)−0.0093 (6)0.0065 (5)−0.0016 (6)
O10.0973 (10)0.0948 (10)0.0405 (6)−0.0258 (8)0.0023 (6)−0.0124 (6)
O20.0806 (8)0.1016 (10)0.0368 (6)−0.0258 (7)0.0128 (5)−0.0003 (6)

Geometric parameters (Å, °)

C1—N11.3651 (19)C9—C101.381 (3)
C1—C141.4079 (19)C9—H90.9300
C1—C21.4133 (19)C10—C111.394 (2)
C2—C31.366 (2)C10—H100.9300
C2—H20.9300C11—C121.491 (2)
C3—C41.3970 (19)C12—O21.2138 (17)
C3—H30.9300C12—C131.4939 (19)
C4—C131.3987 (18)C13—C141.385 (2)
C4—C51.459 (2)C14—H140.9300
C5—O11.2208 (17)C15—N11.449 (2)
C5—C61.490 (2)C15—H15A0.9600
C6—C111.392 (2)C15—H15B0.9600
C6—C71.396 (2)C15—H15C0.9600
C7—C81.380 (3)C16—N11.444 (2)
C7—H70.9300C16—H16A0.9600
C8—C91.370 (3)C16—H16B0.9600
C8—H80.9300C16—H16C0.9600
N1—C1—C14121.85 (12)C11—C10—H10120.0
N1—C1—C2120.95 (13)C6—C11—C10119.66 (14)
C14—C1—C2117.20 (13)C6—C11—C12121.08 (13)
C3—C2—C1121.02 (13)C10—C11—C12119.26 (14)
C3—C2—H2119.5O2—C12—C11120.97 (13)
C1—C2—H2119.5O2—C12—C13121.60 (14)
C2—C3—C4121.89 (12)C11—C12—C13117.43 (12)
C2—C3—H3119.1C14—C13—C4120.94 (12)
C4—C3—H3119.1C14—C13—C12118.73 (12)
C3—C4—C13117.77 (13)C4—C13—C12120.33 (13)
C3—C4—C5119.92 (12)C13—C14—C1121.15 (12)
C13—C4—C5122.31 (13)C13—C14—H14119.4
O1—C5—C4121.78 (14)C1—C14—H14119.4
O1—C5—C6120.58 (14)N1—C15—H15A109.5
C4—C5—C6117.64 (12)N1—C15—H15B109.5
C11—C6—C7119.56 (14)H15A—C15—H15B109.5
C11—C6—C5121.20 (13)N1—C15—H15C109.5
C7—C6—C5119.23 (14)H15A—C15—H15C109.5
C8—C7—C6119.71 (17)H15B—C15—H15C109.5
C8—C7—H7120.1N1—C16—H16A109.5
C6—C7—H7120.1N1—C16—H16B109.5
C9—C8—C7120.86 (17)H16A—C16—H16B109.5
C9—C8—H8119.6N1—C16—H16C109.5
C7—C8—H8119.6H16A—C16—H16C109.5
C8—C9—C10120.12 (16)H16B—C16—H16C109.5
C8—C9—H9119.9C1—N1—C16120.78 (13)
C10—C9—H9119.9C1—N1—C15120.72 (12)
C9—C10—C11120.08 (17)C16—N1—C15117.68 (13)
C9—C10—H10120.0
N1—C1—C2—C3178.16 (13)C9—C10—C11—C60.1 (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—C131.3 (2)C10—C11—C12—O2−0.4 (2)
C2—C3—C4—C5−178.30 (14)C6—C11—C12—C130.4 (2)
C3—C4—C5—O11.6 (2)C10—C11—C12—C13179.92 (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—C14178.97 (13)
C13—C4—C5—C61.0 (2)C3—C4—C13—C12179.82 (12)
O1—C5—C6—C11178.32 (15)C5—C4—C13—C12−0.5 (2)
C4—C5—C6—C11−0.7 (2)O2—C12—C13—C140.6 (2)
O1—C5—C6—C7−1.4 (2)C11—C12—C13—C14−179.66 (12)
C4—C5—C6—C7179.60 (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—C8179.16 (15)C4—C13—C14—C1−0.9 (2)
C6—C7—C8—C90.6 (3)C12—C13—C14—C1178.63 (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—C131.7 (2)
C7—C6—C11—C100.2 (2)C14—C1—N1—C16−10.0 (2)
C5—C6—C11—C10−179.49 (13)C2—C1—N1—C16170.79 (14)
C7—C6—C11—C12179.74 (13)C14—C1—N1—C15−179.41 (14)
C5—C6—C11—C120.0 (2)C2—C1—N1—C151.4 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C9—H9···O1i0.932.503.272 (2)140

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG5045).

References

  • Bruker (1997). SMART Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (1999). SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Havlik, M., Kral, V., Kaplanek, R. & Dolensky, B. (2008). Org. Lett.10, 4767–4769. [PubMed]
  • Janczak, J. (1995). Acta Cryst. C51, 1381–1382.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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