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Acta Crystallogr Sect E Struct Rep Online. 2010 May 1; 66(Pt 5): o1117.
Published online 2010 April 21. doi:  10.1107/S1600536810013310
PMCID: PMC2979029

1-(2-Methoxy­anilino)anthraquinone

Abstract

In the title compound, C21H15NO3, the dihedral angle formed between the aromatic ring systems is 71.50 (3)°. The meth­oxy group is coplanar with the benzene ring to which it is connected, the C—O—C—C torsion angle being 6.37 (17)°. The observed conformation is stabilized by an intra­molecular N—H(...)O hydrogen bond, generating an S(6) ring.

Related literature

For background to anthraquinone derivatives, see: Matsui (1998 [triangle]); Rao & Choudhary (1990 [triangle]).

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Object name is e-66-o1117-scheme1.jpg

Experimental

Crystal data

  • C21H15NO3
  • M r = 329.34
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1117-efi1.jpg
  • a = 11.4222 (3) Å
  • b = 7.9878 (2) Å
  • c = 16.9332 (4) Å
  • β = 100.9851 (12)°
  • V = 1516.65 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 110 K
  • 0.40 × 0.30 × 0.14 mm

Data collection

  • Bruker–Nonius X8 APEXII diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2006 [triangle]) T min = 0.962, T max = 0.987
  • 32405 measured reflections
  • 5620 independent reflections
  • 3863 reflections with I > 2σ(I)
  • R int = 0.031

Refinement

  • R[F 2 > 2σ(F 2)] = 0.052
  • wR(F 2) = 0.161
  • S = 1.05
  • 5620 reflections
  • 286 parameters
  • All H-atom parameters refined
  • Δρmax = 0.49 e Å−3
  • Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2006 [triangle]); cell refinement: SAINT (Bruker, 2006 [triangle]); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1994 [triangle]); program(s) used to refine structure: XL (Bruker, 2004 [triangle]); molecular graphics: XL; software used to prepare material for publication: XL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810013310/tk2648sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810013310/tk2648Isup2.hkl

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

Acknowledgments

This research was supported by the China Scholarship Council (No. 2007102249). We also wish to thank Dr Harold S. Freeman and Dr Paul Boyle at North Carolina State University for their help.

supplementary crystallographic information

Comment

Anthraquinone and its derivatives are important compounds in the fields of dyes and pigments (Matsui 1998; Rao & Choudhary, 1990). Here, we report the crystal structure of the title compound, (I), Fig. 1. The dihedral angle formed between the aromatic systems is 71.50 (3)°. The methoxy group is co-planar with the benzene ring to which it is connected with the C21–O3–C16–C17 torsion angle being 6.37 (17) °. The observed conformation is stabilised by an intramolecular N–H···O hydrogen bond, Table 1.

Experimental

The crystal was obtained by dissolving (I) in methyl acetate (50 ml) and leaving the resulting solution, which was covered with Parafilm plastic containing pin holes, to evaporate at room temperature.

Refinement

The hydrogen atoms were refined freely: N–H = 0.932 (19) Å, and C–H = 0.937 (16)–1.051 (17) Å.

Figures

Fig. 1.
The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.

Crystal data

C21H15NO3F(000) = 688
Mr = 329.34Dx = 1.442 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ybcCell parameters from 8857 reflections
a = 11.4222 (3) Åθ = 2.8–31.7°
b = 7.9878 (2) ŵ = 0.10 mm1
c = 16.9332 (4) ÅT = 110 K
β = 100.9851 (12)°Prism, red
V = 1516.65 (7) Å30.40 × 0.30 × 0.14 mm
Z = 4

Data collection

Bruker–Nonius X8 APEXII diffractometer5620 independent reflections
Radiation source: fine-focus sealed tube3863 reflections with I > 2σ(I)
graphiteRint = 0.031
[var phi] scansθmax = 34.9°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2006)h = −17→16
Tmin = 0.962, Tmax = 0.987k = −12→11
32405 measured reflectionsl = −24→25

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)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161All H-atom parameters refined
S = 1.05w = 1/[σ2(Fo2) + (0.0934P)2 + 0.1215P] where P = (Fo2 + 2Fc2)/3
5620 reflections(Δ/σ)max = 0.001
286 parametersΔρmax = 0.49 e Å3
0 restraintsΔρmin = −0.20 e Å3

Special details

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.
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
O10.13993 (7)0.20278 (10)0.63675 (5)0.02712 (19)
O2−0.22023 (8)−0.23872 (11)0.55875 (5)0.0302 (2)
O30.46774 (7)−0.06574 (11)0.66601 (4)0.0286 (2)
N10.26972 (8)−0.02097 (13)0.72798 (6)0.0258 (2)
H10.2651 (17)0.076 (2)0.6971 (11)0.058 (5)*
C10.05822 (9)0.09907 (14)0.62187 (6)0.0203 (2)
C20.06875 (9)−0.07113 (13)0.65401 (6)0.0192 (2)
C30.17497 (9)−0.12548 (14)0.70664 (6)0.0216 (2)
C40.18047 (11)−0.29225 (15)0.73478 (6)0.0263 (2)
H40.2586 (12)−0.3278 (18)0.7699 (8)0.030 (4)*
C50.08556 (11)−0.39923 (16)0.71402 (7)0.0279 (3)
H50.0911 (14)−0.524 (2)0.7336 (10)0.043 (4)*
C6−0.02007 (11)−0.34632 (15)0.66463 (6)0.0248 (2)
H6−0.0882 (13)−0.4234 (19)0.6527 (9)0.034 (4)*
C7−0.02689 (9)−0.18511 (14)0.63397 (6)0.0201 (2)
C8−0.13910 (9)−0.13774 (14)0.57762 (6)0.0214 (2)
C9−0.14902 (9)0.03492 (14)0.54568 (6)0.0198 (2)
C10−0.25212 (10)0.08461 (15)0.49214 (6)0.0232 (2)
H10−0.3179 (11)−0.0046 (17)0.4743 (7)0.020 (3)*
C11−0.26221 (10)0.24721 (15)0.46310 (6)0.0249 (2)
H11−0.3326 (12)0.2845 (18)0.4248 (8)0.029 (3)*
C12−0.17056 (10)0.36132 (15)0.48686 (6)0.0242 (2)
H12−0.1783 (13)0.481 (2)0.4670 (9)0.038 (4)*
C13−0.06699 (10)0.31181 (14)0.53857 (6)0.0222 (2)
H13−0.0034 (14)0.387 (2)0.5534 (9)0.037 (4)*
C14−0.05540 (9)0.14870 (13)0.56821 (5)0.0189 (2)
C150.37851 (10)−0.06745 (14)0.77938 (6)0.0240 (2)
C160.48166 (10)−0.08838 (14)0.74715 (6)0.0227 (2)
C170.58900 (10)−0.12904 (15)0.79741 (7)0.0265 (2)
H170.6567 (14)−0.143 (2)0.7741 (9)0.038 (4)*
C180.59215 (11)−0.15392 (16)0.87909 (7)0.0297 (3)
H180.6648 (14)−0.188 (2)0.9122 (10)0.043 (4)*
C190.49073 (12)−0.13533 (17)0.91119 (7)0.0327 (3)
H190.4947 (14)−0.153 (2)0.9695 (10)0.048 (5)*
C200.38352 (12)−0.09066 (17)0.86123 (7)0.0315 (3)
H200.3124 (14)−0.0724 (19)0.8831 (9)0.035 (4)*
C210.56705 (12)−0.10204 (19)0.62942 (7)0.0329 (3)
H21A0.6315 (16)−0.015 (2)0.6472 (11)0.048 (4)*
H21B0.5396 (15)−0.094 (2)0.5726 (11)0.047 (4)*
H21C0.6026 (15)−0.216 (2)0.6451 (10)0.048 (5)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0201 (4)0.0221 (4)0.0365 (4)−0.0035 (3)−0.0012 (3)0.0040 (3)
O20.0269 (4)0.0259 (5)0.0363 (4)−0.0078 (3)0.0020 (3)−0.0011 (3)
O30.0257 (4)0.0362 (5)0.0235 (4)0.0020 (3)0.0038 (3)0.0023 (3)
N10.0191 (4)0.0260 (5)0.0305 (4)0.0014 (4)0.0001 (3)0.0068 (4)
C10.0180 (5)0.0207 (5)0.0221 (4)−0.0002 (4)0.0040 (3)0.0001 (4)
C20.0193 (5)0.0189 (5)0.0204 (4)0.0014 (4)0.0059 (3)0.0007 (4)
C30.0204 (5)0.0232 (6)0.0224 (4)0.0015 (4)0.0064 (3)0.0015 (4)
C40.0272 (6)0.0256 (6)0.0262 (5)0.0045 (4)0.0058 (4)0.0066 (4)
C50.0342 (6)0.0232 (6)0.0277 (5)0.0009 (5)0.0090 (4)0.0060 (4)
C60.0298 (6)0.0206 (6)0.0256 (5)−0.0033 (5)0.0089 (4)0.0015 (4)
C70.0217 (5)0.0199 (5)0.0201 (4)−0.0002 (4)0.0075 (3)−0.0013 (4)
C80.0213 (5)0.0209 (5)0.0230 (4)−0.0018 (4)0.0066 (3)−0.0025 (4)
C90.0194 (5)0.0204 (5)0.0204 (4)−0.0006 (4)0.0054 (3)−0.0027 (4)
C100.0196 (5)0.0252 (6)0.0244 (4)−0.0006 (4)0.0034 (4)−0.0027 (4)
C110.0208 (5)0.0280 (6)0.0250 (4)0.0025 (4)0.0018 (4)−0.0017 (4)
C120.0233 (5)0.0218 (6)0.0269 (5)0.0032 (4)0.0037 (4)0.0007 (4)
C130.0203 (5)0.0206 (5)0.0254 (4)−0.0011 (4)0.0038 (4)−0.0013 (4)
C140.0172 (5)0.0195 (5)0.0204 (4)0.0004 (4)0.0042 (3)−0.0013 (4)
C150.0217 (5)0.0235 (6)0.0251 (4)0.0016 (4)0.0002 (4)0.0023 (4)
C160.0231 (5)0.0193 (5)0.0243 (4)0.0002 (4)0.0014 (4)−0.0006 (4)
C170.0207 (5)0.0243 (6)0.0323 (5)0.0000 (4)−0.0007 (4)−0.0004 (4)
C180.0280 (6)0.0256 (6)0.0305 (5)0.0007 (5)−0.0069 (4)−0.0006 (4)
C190.0383 (7)0.0342 (7)0.0232 (5)0.0031 (5)−0.0002 (4)0.0014 (4)
C200.0312 (6)0.0365 (7)0.0270 (5)0.0047 (5)0.0059 (4)0.0031 (5)
C210.0300 (6)0.0394 (8)0.0307 (5)−0.0020 (6)0.0094 (5)−0.0037 (5)

Geometric parameters (Å, °)

O1—C11.2374 (13)C10—C111.3858 (17)
O2—C81.2241 (13)C10—H101.038 (13)
O3—C161.3647 (13)C11—C121.3886 (16)
O3—C211.4222 (15)C11—H110.978 (14)
N1—C31.3600 (15)C12—C131.3884 (14)
N1—C151.4238 (13)C12—H121.009 (16)
N1—H10.932 (19)C13—C141.3934 (15)
C1—C21.4608 (15)C13—H130.937 (16)
C1—C141.4892 (14)C15—C201.3887 (16)
C2—C71.4128 (15)C15—C161.3996 (16)
C2—C31.4293 (14)C16—C171.3912 (15)
C3—C41.4122 (16)C17—C181.3910 (16)
C4—C51.3726 (17)C17—H170.940 (16)
C4—H41.014 (14)C18—C191.3782 (19)
C5—C61.3961 (16)C18—H180.948 (16)
C5—H51.051 (17)C19—C201.3956 (17)
C6—C71.3851 (16)C19—H190.990 (17)
C6—H60.983 (15)C20—H200.966 (16)
C7—C81.4933 (14)C21—H21A1.016 (18)
C8—C91.4779 (16)C21—H21B0.955 (18)
C9—C141.3998 (14)C21—H21C1.013 (18)
C9—C101.3998 (14)
C16—O3—C21117.52 (9)C10—C11—H11121.5 (8)
C3—N1—C15124.05 (10)C12—C11—H11118.1 (8)
C3—N1—H1113.9 (12)C13—C12—C11120.03 (11)
C15—N1—H1120.7 (12)C13—C12—H12119.3 (9)
O1—C1—C2122.81 (9)C11—C12—H12120.6 (9)
O1—C1—C14118.80 (10)C12—C13—C14120.30 (10)
C2—C1—C14118.38 (9)C12—C13—H13120.7 (10)
C7—C2—C3118.67 (9)C14—C13—H13119.0 (10)
C7—C2—C1120.35 (9)C13—C14—C9119.59 (9)
C3—C2—C1120.99 (9)C13—C14—C1118.73 (9)
N1—C3—C4120.49 (10)C9—C14—C1121.67 (9)
N1—C3—C2121.15 (10)C20—C15—C16119.71 (10)
C4—C3—C2118.35 (10)C20—C15—N1120.68 (11)
C5—C4—C3121.24 (10)C16—C15—N1119.61 (9)
C5—C4—H4122.7 (8)O3—C16—C17124.53 (11)
C3—C4—H4116.1 (8)O3—C16—C15115.56 (9)
C4—C5—C6121.01 (11)C17—C16—C15119.91 (10)
C4—C5—H5120.9 (9)C18—C17—C16119.63 (11)
C6—C5—H5118.0 (9)C18—C17—H17122.3 (9)
C7—C6—C5119.11 (11)C16—C17—H17118.0 (9)
C7—C6—H6121.3 (9)C19—C18—C17120.82 (10)
C5—C6—H6119.6 (9)C19—C18—H18120.3 (10)
C6—C7—C2121.56 (9)C17—C18—H18118.9 (10)
C6—C7—C8117.08 (10)C18—C19—C20119.67 (11)
C2—C7—C8121.36 (9)C18—C19—H19119.7 (10)
O2—C8—C9121.19 (10)C20—C19—H19120.6 (10)
O2—C8—C7120.98 (10)C15—C20—C19120.24 (12)
C9—C8—C7117.83 (9)C15—C20—H20119.0 (9)
C14—C9—C10119.81 (10)C19—C20—H20120.7 (9)
C14—C9—C8120.32 (9)O3—C21—H21A108.9 (10)
C10—C9—C8119.87 (10)O3—C21—H21B106.8 (10)
C11—C10—C9119.89 (10)H21A—C21—H21B109.4 (15)
C11—C10—H10122.2 (7)O3—C21—H21C112.5 (10)
C9—C10—H10117.8 (7)H21A—C21—H21C107.9 (13)
C10—C11—C12120.35 (10)H21B—C21—H21C111.3 (14)
O1—C1—C2—C7−179.01 (10)C8—C9—C10—C11179.05 (9)
C14—C1—C2—C70.30 (14)C9—C10—C11—C12−0.04 (16)
O1—C1—C2—C31.50 (16)C10—C11—C12—C131.45 (17)
C14—C1—C2—C3−179.20 (9)C11—C12—C13—C14−1.36 (16)
C15—N1—C3—C4−0.72 (17)C12—C13—C14—C9−0.14 (16)
C15—N1—C3—C2−179.32 (10)C12—C13—C14—C1178.47 (9)
C7—C2—C3—N1−179.95 (10)C10—C9—C14—C131.55 (15)
C1—C2—C3—N1−0.44 (16)C8—C9—C14—C13−178.96 (9)
C7—C2—C3—C41.43 (15)C10—C9—C14—C1−177.02 (9)
C1—C2—C3—C4−179.07 (9)C8—C9—C14—C12.46 (15)
N1—C3—C4—C5179.81 (11)O1—C1—C14—C13−1.90 (15)
C2—C3—C4—C5−1.55 (16)C2—C1—C14—C13178.77 (9)
C3—C4—C5—C6−0.36 (18)O1—C1—C14—C9176.69 (10)
C4—C5—C6—C72.38 (17)C2—C1—C14—C9−2.64 (15)
C5—C6—C7—C2−2.49 (16)C3—N1—C15—C20−71.76 (16)
C5—C6—C7—C8176.51 (9)C3—N1—C15—C16108.85 (13)
C3—C2—C7—C60.58 (15)C21—O3—C16—C176.37 (17)
C1—C2—C7—C6−178.92 (9)C21—O3—C16—C15−173.84 (11)
C3—C2—C7—C8−178.37 (9)C20—C15—C16—O3178.95 (11)
C1—C2—C7—C82.13 (15)N1—C15—C16—O3−1.66 (16)
C6—C7—C8—O2−1.10 (15)C20—C15—C16—C17−1.25 (18)
C2—C7—C8—O2177.90 (10)N1—C15—C16—C17178.14 (11)
C6—C7—C8—C9178.70 (9)O3—C16—C17—C18−178.15 (11)
C2—C7—C8—C9−2.30 (14)C15—C16—C17—C182.07 (18)
O2—C8—C9—C14179.78 (10)C16—C17—C18—C19−1.38 (19)
C7—C8—C9—C14−0.03 (14)C17—C18—C19—C20−0.1 (2)
O2—C8—C9—C10−0.74 (15)C16—C15—C20—C19−0.27 (19)
C7—C8—C9—C10179.46 (9)N1—C15—C20—C19−179.65 (12)
C14—C9—C10—C11−1.46 (16)C18—C19—C20—C151.0 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O10.932 (19)1.886 (18)2.6279 (13)135.0 (17)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2648).

References

  • Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst.27, 435.
  • Bruker (2004). XL Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2006). SADABS, APEX2 and SAINT Madison, Wisconsin, USA.
  • Matsui, M. (1998). Dyes Pigments, 40, 21–26.
  • Rao, B. V. & Choudhary, V. (1990). J. Soc. Dyers Colour.106, 388–394.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography