organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

1-Meth­­oxy-11H-benzo[b]fluoren-11-one

aDepartment of Chemical Engineering, Feng Chia University, 40724 Taichung, Taiwan
*Correspondence e-mail: kyuchen@fcu.edu.tw

(Received 5 October 2012; accepted 7 December 2012; online 12 December 2012)

In the title compound, C18H12O2, the non-H atoms are nearly coplanar, the maximum atomic deviation being 0.113 (2) Å. ππ stacking is observed in the crystal structure, the shortest centroid–centroid distance being 3.5983 (19) Å. The mol­ecular packing is further stabilized by weak C—H⋯O hydrogen bonds, forming an infinite chain along [100] and generating a C(6) motif.

Related literature

For the preparation of the title compound, see: Tang et al. (2011[Tang, K.-C., Chang, M.-J., Lin, T.-Y., Pan, H.-A., Fang, T.-C., Chen, K.-Y., Hung, W.-Y., Hsu, Y.-H. & Chou, P.-T. (2011). J. Am. Chem. Soc. 133, 17738-17745.]). For applications of indanone derivatives, see: Borbone et al. (2011[Borbone, F., Carella, A., Ricciotti, L., Tuzi, A., Roviello, A. & Barsella, A. (2011). Dyes Pigm. 88, 290-295.]); Borge et al. (2010[Borge, J., Cadierno, V., Díez, J., García-Garrido, S. E. & Gimeno, J. (2010). Dyes Pigm. 87, 209-217.]); Cai & Dolbier (2005[Cai, X., Wu, K. & Dolbier, W. R. Jr (2005). J. Fluorine Chem. 126, 479-482.]); Cui et al. (2009[Cui, Y., Ren, H., Yu, J., Wang, Z. & Qian, G. (2009). Dyes Pigm. 81, 53-57.]); Fu & Wang (2008[Fu, T.-L. & Wang, I.-J. (2008). Dyes Pigm. 76, 590-595.]); Li et al. (2009[Li, X., Kim, S. H. & Son, Y. A. (2009). Dyes Pigm. 82, 293-298.]); Rahman et al. (2011[Rahman, A., Zahrani, S. M. A. & Ajjou, A. A. N. (2011). Chin. Chem. Lett. 22, 691-693.]); Sousa et al. (2011[Sousa, C. M., Berthet, J., Delbaere, S. & Coelho, P. J. (2011). Dyes Pigm. 92, 537-541.]); Yu et al. (2011[Yu, S.-B., Liu, H.-M., Luo, Y. & Lu, W. (2011). Chin. Chem. Lett. 22, 264-267.]). For related structures, see: Chang & Chen (2012[Chang, Y. J. & Chen, K.-Y. (2012). Acta Cryst. E68, o3063.]); Chen et al. (2011a[Chen, K.-Y., Fang, T.-C. & Chang, M.-J. (2011a). Acta Cryst. E67, o992.],b[Chen, K.-Y., Wen, Y.-S., Fang, T.-C., Chang, Y.-J. & Chang, M.-J. (2011b). Acta Cryst. E67, o927.]).

[Scheme 1]

Experimental

Crystal data
  • C18H12O2

  • Mr = 260.28

  • Monoclinic, P 21 /c

  • a = 7.7202 (3) Å

  • b = 9.2462 (4) Å

  • c = 18.0294 (8) Å

  • β = 99.935 (2)°

  • V = 1267.68 (9) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 299 K

  • 0.50 × 0.47 × 0.20 mm

Data collection
  • Bruker SMART CCD detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.957, Tmax = 0.983

  • 11580 measured reflections

  • 2559 independent reflections

  • 1881 reflections with I > 2σ(I)

  • Rint = 0.042

Refinement
  • R[F2 > 2σ(F2)] = 0.083

  • wR(F2) = 0.250

  • S = 1.11

  • 2559 reflections

  • 183 parameters

  • H-atom parameters constrained

  • Δρmax = 0.49 e Å−3

  • Δρmin = −0.42 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C7—H7⋯O1i 0.93 2.57 3.299 (5) 135
C11—H11⋯O1ii 0.93 2.55 3.298 (4) 138
Symmetry codes: (i) [-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) x-1, y, z.

Data collection: SMART (Bruker, 2005[Bruker (2005). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).

Supporting information


Comment top

Indanone and its derivatives are some of the most widely used organic compounds (Rahman et al., 2011). They are used as pigments and dyes (Cui et al., 2009; Li et al., 2009), intermediates in organic synthesis (Borbone et al., 2011; Borge et al., 2010; Fu & Wang, 2008; Yu et al., 2011) and exhibit a wide variety of biological activities (Sousa et al., 2011). In addition, 1-indanones were important precursors in the regiospecific synthesis of 2-fluoro-1-naphthols (Cai et al., 2005).

The molecular structure of the title compound comprises a 7-methoxy-1-indanone unit having a naphthalene ring fused on one side (Fig. 1). The 1-indaneone moiety is essentially planar (r.m.s. deviation = 0.0075 Å), which is consistent with previous studies (Chang & Chen, 2012; Chen et al., 2011a,b). ππ stacking is observed between the tetracyclic plane and its adjacent one, the closest centroid-centroid distance being 3.5983 (19) Å [symmetry code: 2 - x, -y, 2 - z]. The molecular packing (Fig. 2) is further stabilized by weak non-classical intermolecular C—H···O hydrogen bonds (Table 1).

Related literature top

For the preparation of the title compound, see: Tang et al. (2011). For applications of indanone derivatives, see: Borbone et al. (2011); Borge et al. (2010); Cai et al. (2005); Cui et al. (2009); Fu & Wang (2008); Li et al. (2009); Rahman et al. (2011); Sousa et al. (2011); Yu et al. (2011). For related structures, see: Chang & Chen (2012); Chen et al. (2011a,b).

Experimental top

The title compound was synthesized according to the literature (Tang et al., 2011). Yellow parallelepiped-shaped crystals suitable for the crystallographic studies reported here were isolated over a period of six weeks by slow evaporation from a chloroform solution.

Refinement top

The C bound H atoms were positioned geometrically (C—H = 0.93–0.96 Å) and allowed to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: SMART (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. A section of the crystal packing of the title compound, viewed down the c axis. Blue and green dashed lines denote the intermolecular C7—H7···O1 and C11—H11···O1 hydrogen bonds, respectively.
1-Methoxy-11H-benzo[b]fluoren-11-one top
Crystal data top
C18H12O2F(000) = 544
Mr = 260.28Dx = 1.364 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6867 reflections
a = 7.7202 (3) Åθ = 2.7–26.4°
b = 9.2462 (4) ŵ = 0.09 mm1
c = 18.0294 (8) ÅT = 299 K
β = 99.935 (2)°Parallelepiped, yellow
V = 1267.68 (9) Å30.50 × 0.47 × 0.20 mm
Z = 4
Data collection top
Bruker SMART CCD detector
diffractometer
2559 independent reflections
Radiation source: fine-focus sealed tube1881 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
ϕ and ω scansθmax = 26.4°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 99
Tmin = 0.957, Tmax = 0.983k = 1110
11580 measured reflectionsl = 2221
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.083H-atom parameters constrained
wR(F2) = 0.250 w = 1/[σ2(Fo2) + (0.1046P)2 + 1.682P]
where P = (Fo2 + 2Fc2)/3
S = 1.11(Δ/σ)max < 0.001
2559 reflectionsΔρmax = 0.49 e Å3
183 parametersΔρmin = 0.42 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.041 (7)
Crystal data top
C18H12O2V = 1267.68 (9) Å3
Mr = 260.28Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.7202 (3) ŵ = 0.09 mm1
b = 9.2462 (4) ÅT = 299 K
c = 18.0294 (8) Å0.50 × 0.47 × 0.20 mm
β = 99.935 (2)°
Data collection top
Bruker SMART CCD detector
diffractometer
2559 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
1881 reflections with I > 2σ(I)
Tmin = 0.957, Tmax = 0.983Rint = 0.042
11580 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0830 restraints
wR(F2) = 0.250H-atom parameters constrained
S = 1.11Δρmax = 0.49 e Å3
2559 reflectionsΔρmin = 0.42 e Å3
183 parameters
Special details top

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) top
xyzUiso*/Ueq
O11.2838 (3)0.3051 (3)0.92283 (15)0.0675 (8)
O21.3420 (3)0.0972 (3)1.04942 (14)0.0571 (7)
C11.0841 (4)0.2264 (3)1.00540 (17)0.0428 (7)
C21.1419 (4)0.3058 (4)0.94252 (18)0.0464 (8)
C30.9836 (4)0.3911 (3)0.90635 (17)0.0439 (7)
C40.9640 (4)0.4820 (4)0.84656 (18)0.0490 (8)
H41.05710.49780.82090.059*
C50.8006 (4)0.5531 (3)0.82323 (17)0.0461 (8)
C60.7726 (5)0.6517 (4)0.7623 (2)0.0579 (9)
H60.86340.67120.73600.069*
C70.6147 (6)0.7183 (4)0.7419 (2)0.0683 (11)
H70.59900.78350.70200.082*
C80.4773 (6)0.6901 (4)0.7796 (2)0.0694 (11)
H80.36960.73590.76460.083*
C90.4978 (5)0.5959 (4)0.8385 (2)0.0578 (9)
H90.40380.57800.86330.069*
C100.6602 (4)0.5249 (3)0.86266 (19)0.0475 (8)
C110.6857 (4)0.4280 (3)0.92502 (19)0.0473 (8)
H110.59370.40890.95080.057*
C120.8438 (4)0.3637 (3)0.94670 (17)0.0401 (7)
C130.9079 (4)0.2608 (3)1.00807 (17)0.0420 (7)
C140.8220 (4)0.2001 (4)1.0611 (2)0.0522 (8)
H140.70520.22241.06250.063*
C150.9155 (5)0.1040 (4)1.1126 (2)0.0589 (9)
H150.86000.06261.14930.071*
C161.0877 (5)0.0687 (4)1.1106 (2)0.0544 (9)
H161.14650.00401.14580.065*
C171.1749 (4)0.1289 (4)1.05646 (18)0.0471 (8)
C181.4337 (5)0.0107 (4)1.0985 (2)0.0627 (10)
H18A1.45450.02481.14930.094*
H18B1.54400.03211.08320.094*
H18C1.36380.09711.09580.094*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0431 (14)0.087 (2)0.0777 (18)0.0056 (12)0.0246 (12)0.0121 (15)
O20.0438 (13)0.0598 (16)0.0666 (16)0.0075 (11)0.0062 (11)0.0054 (12)
C10.0410 (16)0.0411 (16)0.0463 (16)0.0028 (13)0.0079 (12)0.0059 (13)
C20.0366 (16)0.0548 (19)0.0490 (17)0.0035 (13)0.0105 (13)0.0041 (14)
C30.0381 (16)0.0436 (17)0.0502 (17)0.0034 (12)0.0086 (12)0.0051 (13)
C40.0439 (17)0.053 (2)0.0506 (18)0.0039 (14)0.0105 (13)0.0026 (14)
C50.0506 (18)0.0394 (17)0.0468 (17)0.0019 (13)0.0040 (13)0.0069 (13)
C60.069 (2)0.051 (2)0.0510 (19)0.0002 (17)0.0046 (16)0.0012 (15)
C70.085 (3)0.054 (2)0.060 (2)0.012 (2)0.003 (2)0.0058 (18)
C80.070 (3)0.057 (2)0.073 (2)0.0191 (19)0.009 (2)0.0058 (19)
C90.0480 (19)0.056 (2)0.067 (2)0.0071 (16)0.0021 (16)0.0088 (17)
C100.0422 (17)0.0401 (17)0.0579 (18)0.0022 (13)0.0023 (13)0.0100 (14)
C110.0393 (16)0.0428 (18)0.0606 (19)0.0022 (13)0.0105 (13)0.0071 (14)
C120.0355 (15)0.0377 (16)0.0478 (16)0.0042 (12)0.0095 (12)0.0070 (12)
C130.0426 (16)0.0360 (16)0.0486 (16)0.0038 (12)0.0113 (12)0.0073 (12)
C140.0449 (18)0.055 (2)0.0601 (19)0.0025 (14)0.0189 (14)0.0008 (16)
C150.065 (2)0.058 (2)0.058 (2)0.0087 (17)0.0212 (17)0.0047 (17)
C160.058 (2)0.052 (2)0.0530 (19)0.0010 (16)0.0095 (15)0.0011 (15)
C170.0447 (17)0.0449 (18)0.0511 (17)0.0018 (13)0.0064 (13)0.0043 (14)
C180.053 (2)0.056 (2)0.074 (2)0.0063 (16)0.0035 (17)0.0071 (18)
Geometric parameters (Å, º) top
O1—C21.208 (4)C8—H80.9300
O2—C171.350 (4)C9—C101.416 (5)
O2—C181.436 (4)C9—H90.9300
C1—C171.389 (5)C10—C111.425 (5)
C1—C131.406 (4)C11—C121.354 (4)
C1—C21.483 (4)C11—H110.9300
C2—C31.505 (4)C12—C131.478 (4)
C3—C41.355 (5)C13—C141.374 (4)
C3—C121.424 (4)C14—C151.394 (5)
C4—C51.421 (5)C14—H140.9300
C4—H40.9300C15—C161.375 (5)
C5—C61.415 (5)C15—H150.9300
C5—C101.419 (5)C16—C171.394 (5)
C6—C71.359 (5)C16—H160.9300
C6—H60.9300C18—H18A0.9600
C7—C81.379 (6)C18—H18B0.9600
C7—H70.9300C18—H18C0.9600
C8—C91.363 (6)
C17—O2—C18118.0 (3)C9—C10—C11121.9 (3)
C17—C1—C13120.3 (3)C5—C10—C11119.8 (3)
C17—C1—C2130.1 (3)C12—C11—C10119.9 (3)
C13—C1—C2109.5 (3)C12—C11—H11120.0
O1—C2—C1129.0 (3)C10—C11—H11120.0
O1—C2—C3125.8 (3)C11—C12—C3120.0 (3)
C1—C2—C3105.2 (3)C11—C12—C13131.9 (3)
C4—C3—C12121.8 (3)C3—C12—C13108.2 (3)
C4—C3—C2129.8 (3)C14—C13—C1121.2 (3)
C12—C3—C2108.4 (3)C14—C13—C12130.1 (3)
C3—C4—C5119.6 (3)C1—C13—C12108.7 (3)
C3—C4—H4120.2C13—C14—C15117.9 (3)
C5—C4—H4120.2C13—C14—H14121.1
C6—C5—C10118.7 (3)C15—C14—H14121.1
C6—C5—C4122.4 (3)C16—C15—C14121.8 (3)
C10—C5—C4118.9 (3)C16—C15—H15119.1
C7—C6—C5120.8 (4)C14—C15—H15119.1
C7—C6—H6119.6C15—C16—C17120.6 (3)
C5—C6—H6119.6C15—C16—H16119.7
C6—C7—C8120.8 (4)C17—C16—H16119.7
C6—C7—H7119.6O2—C17—C1117.4 (3)
C8—C7—H7119.6O2—C17—C16124.3 (3)
C9—C8—C7120.6 (4)C1—C17—C16118.3 (3)
C9—C8—H8119.7O2—C18—H18A109.5
C7—C8—H8119.7O2—C18—H18B109.5
C8—C9—C10120.9 (4)H18A—C18—H18B109.5
C8—C9—H9119.5O2—C18—H18C109.5
C10—C9—H9119.5H18A—C18—H18C109.5
C9—C10—C5118.2 (3)H18B—C18—H18C109.5
C17—C1—C2—O11.7 (6)C10—C11—C12—C13179.8 (3)
C13—C1—C2—O1179.4 (3)C4—C3—C12—C110.8 (5)
C17—C1—C2—C3178.3 (3)C2—C3—C12—C11179.9 (3)
C13—C1—C2—C30.6 (3)C4—C3—C12—C13179.9 (3)
O1—C2—C3—C40.0 (6)C2—C3—C12—C130.6 (3)
C1—C2—C3—C4180.0 (3)C17—C1—C13—C140.4 (5)
O1—C2—C3—C12179.3 (3)C2—C1—C13—C14179.4 (3)
C1—C2—C3—C120.7 (3)C17—C1—C13—C12178.7 (3)
C12—C3—C4—C50.3 (5)C2—C1—C13—C120.2 (3)
C2—C3—C4—C5178.9 (3)C11—C12—C13—C140.4 (6)
C3—C4—C5—C6178.6 (3)C3—C12—C13—C14178.8 (3)
C3—C4—C5—C101.1 (5)C11—C12—C13—C1179.4 (3)
C10—C5—C6—C70.0 (5)C3—C12—C13—C10.2 (3)
C4—C5—C6—C7179.6 (3)C1—C13—C14—C150.5 (5)
C5—C6—C7—C80.7 (6)C12—C13—C14—C15179.4 (3)
C6—C7—C8—C90.6 (6)C13—C14—C15—C160.7 (5)
C7—C8—C9—C100.1 (6)C14—C15—C16—C170.1 (6)
C8—C9—C10—C50.7 (5)C18—O2—C17—C1175.9 (3)
C8—C9—C10—C11178.8 (3)C18—O2—C17—C163.1 (5)
C6—C5—C10—C90.7 (4)C13—C1—C17—O2178.0 (3)
C4—C5—C10—C9179.7 (3)C2—C1—C17—O20.7 (5)
C6—C5—C10—C11178.9 (3)C13—C1—C17—C161.0 (5)
C4—C5—C10—C110.7 (4)C2—C1—C17—C16179.7 (3)
C9—C10—C11—C12179.2 (3)C15—C16—C17—O2178.2 (3)
C5—C10—C11—C120.3 (5)C15—C16—C17—C10.8 (5)
C10—C11—C12—C31.1 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···O1i0.932.573.299 (5)135
C11—H11···O1ii0.932.553.298 (4)138
Symmetry codes: (i) x+2, y+1/2, z+3/2; (ii) x1, y, z.

Experimental details

Crystal data
Chemical formulaC18H12O2
Mr260.28
Crystal system, space groupMonoclinic, P21/c
Temperature (K)299
a, b, c (Å)7.7202 (3), 9.2462 (4), 18.0294 (8)
β (°) 99.935 (2)
V3)1267.68 (9)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.50 × 0.47 × 0.20
Data collection
DiffractometerBruker SMART CCD detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.957, 0.983
No. of measured, independent and
observed [I > 2σ(I)] reflections
11580, 2559, 1881
Rint0.042
(sin θ/λ)max1)0.626
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.083, 0.250, 1.11
No. of reflections2559
No. of parameters183
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.49, 0.42

Computer programs: SMART (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···O1i0.932.573.299 (5)135
C11—H11···O1ii0.932.553.298 (4)138
Symmetry codes: (i) x+2, y+1/2, z+3/2; (ii) x1, y, z.
 

Acknowledgements

This work was supported by the National Science Council (grant No. NSC 101–2113-M-035–001-MY2) and Feng Chia University in Taiwan.

References

First citationBorbone, F., Carella, A., Ricciotti, L., Tuzi, A., Roviello, A. & Barsella, A. (2011). Dyes Pigm. 88, 290–295.  Web of Science CSD CrossRef CAS
First citationBorge, J., Cadierno, V., Díez, J., García-Garrido, S. E. & Gimeno, J. (2010). Dyes Pigm. 87, 209–217.  Web of Science CSD CrossRef CAS
First citationBruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationBruker (2005). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationCai, X., Wu, K. & Dolbier, W. R. Jr (2005). J. Fluorine Chem. 126, 479–482.  Web of Science CrossRef CAS
First citationChang, Y. J. & Chen, K.-Y. (2012). Acta Cryst. E68, o3063.  CSD CrossRef IUCr Journals
First citationChen, K.-Y., Fang, T.-C. & Chang, M.-J. (2011a). Acta Cryst. E67, o992.  Web of Science CSD CrossRef IUCr Journals
First citationChen, K.-Y., Wen, Y.-S., Fang, T.-C., Chang, Y.-J. & Chang, M.-J. (2011b). Acta Cryst. E67, o927.  Web of Science CSD CrossRef IUCr Journals
First citationCui, Y., Ren, H., Yu, J., Wang, Z. & Qian, G. (2009). Dyes Pigm. 81, 53–57.  Web of Science CrossRef CAS
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals
First citationFu, T.-L. & Wang, I.-J. (2008). Dyes Pigm. 76, 590–595.  Web of Science CrossRef CAS
First citationLi, X., Kim, S. H. & Son, Y. A. (2009). Dyes Pigm. 82, 293–298.  Web of Science CrossRef CAS
First citationRahman, A., Zahrani, S. M. A. & Ajjou, A. A. N. (2011). Chin. Chem. Lett. 22, 691–693.  Web of Science CrossRef CAS
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSousa, C. M., Berthet, J., Delbaere, S. & Coelho, P. J. (2011). Dyes Pigm. 92, 537–541.  Web of Science CrossRef
First citationTang, K.-C., Chang, M.-J., Lin, T.-Y., Pan, H.-A., Fang, T.-C., Chen, K.-Y., Hung, W.-Y., Hsu, Y.-H. & Chou, P.-T. (2011). J. Am. Chem. Soc. 133, 17738–17745.  Web of Science CSD CrossRef CAS PubMed
First citationYu, S.-B., Liu, H.-M., Luo, Y. & Lu, W. (2011). Chin. Chem. Lett. 22, 264–267.  Web of Science CrossRef CAS

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds