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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

1-[(2-Anilinoeth­yl)iminiometh­yl]-2-naph­thol­ate

aDepartment of Chemistry, Baicheng Normal University, Baicheng 137000, People's Republic of China
*Correspondence e-mail: jyxygzb@163.com

(Received 18 May 2009; accepted 20 May 2009; online 23 May 2009)

The title Schiff base compound, C19H18N2O, was prepared by the reaction of equimolar quanti­ties of 2-hydr­oxy-1-naphthaldehyde with N-phenyl­ethane-1,2-diamine in a methanol solution. The mol­ecule adopts a zwitterionic conformation with the naphthyl OH group deprotonated and the imine N atom protonated. An intra­molecular N—H⋯O hydrogen bond forms between them. The dihedral angle between the benzene ring and the naphthyl system is 86.9 (2)°. In the crystal structure, mol­ecules are linked through inter­molecular N—H⋯O hydrogen bonds, forming chains running along the b axis.

Related literature

For the pharmaceutical and medicinal activity of Schiff bases, see: Dao et al. (2000[Dao, V.-T., Gaspard, C., Mayer, M., Werner, G. H., Nguyen, S. N. & Michelot, R. J. (2000). Eur. J. Med. Chem. 35, 805-813.]); Sriram et al. (2006[Sriram, D., Yogeeswari, P., Myneedu, N. S. & Saraswat, V. (2006). Bioorg. Med. Chem. Lett. 16, 2127-2129.]); Karthikeyan et al. (2006[Karthikeyan, M. S., Prasad, D. J., Poojary, B., Bhat, K. S., Holla, B. S. & Kumari, N. S. (2006). Bioorg. Med. Chem. 14, 7482-7489.]). For Schiff base coordination chemistry, see: Ali et al. (2008[Ali, H. M., Mohamed Mustafa, M. I., Rizal, M. R. & Ng, S. W. (2008). Acta Cryst. E64, m718-m719.]); Kargar et al. (2009[Kargar, H., Jamshidvand, A., Fun, H.-K. & Kia, R. (2009). Acta Cryst. E65, m403-m404.]); Yeap et al. (2009[Yeap, C. S., Kia, R., Kargar, H. & Fun, H.-K. (2009). Acta Cryst. E65, m570-m571.]). For related structures, see: Fun et al. (2009[Fun, H.-K., Kia, R., Vijesh, A. M. & Isloor, A. M. (2009). Acta Cryst. E65, o349-o350.]); Nadeem et al. (2009[Nadeem, S., Shah, M. R. & VanDerveer, D. (2009). Acta Cryst. E65, o897.]); Eltayeb et al. (2008[Eltayeb, N. E., Teoh, S. G., Chantrapromma, S., Fun, H.-K. & Adnan, R. (2008). Acta Cryst. E64, o576-o577.]). For reference structural data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C19H18N2O

  • Mr = 290.35

  • Monoclinic, C c

  • a = 27.511 (3) Å

  • b = 6.845 (2) Å

  • c = 8.543 (2) Å

  • β = 104.263 (2)°

  • V = 1559.2 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 298 K

  • 0.23 × 0.21 × 0.18 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.982, Tmax = 0.986

  • 4485 measured reflections

  • 1753 independent reflections

  • 1312 reflections with I > 2σ(I)

  • Rint = 0.021

Refinement
  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.105

  • S = 1.06

  • 1753 reflections

  • 202 parameters

  • 3 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.18 e Å−3

  • Δρmin = −0.18 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O1 0.907 (10) 1.84 (3) 2.582 (3) 137 (3)
N2—H2⋯O1i 0.86 2.43 3.043 (3) 129
Symmetry code: (i) x, y-1, z.

Data collection: SMART (Bruker, 2002[Bruker (2002). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SAINT and SMART. 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

Schiff base compounds are an important class of materials used in the pharmaceutical and medicinal fields (Dao et al., 2000; Sriram et al., 2006; Karthikeyan et al., 2006). They are also used as versatile ligands in coordination chemistry (Ali et al., 2008; Kargar et al., 2009; Yeap et al., 2009). Recently, the crystal structures of several Schiff base compounds have been reported (Fun et al., 2009; Nadeem et al., 2009; Eltayeb et al., 2008). In this paper, the new Schiff base title compound, (I), Fig. 1, is reported.

In (I), the H atom of the phenol group is transferred to the imine N atom, forming an intramolecular N–H···O hydrogen bond (Table 1). The dihedral angle between the benzene ring and the naphthyl ring is 86.9 (2)°. All the bond lengths are within normal values (Allen et al., 1987). In the crystal structure of the compound, molecules are linked through intermolecular N–H···O hydrogen bonds (Table 1), forming chains running along the b axis (Fig. 2).

Related literature top

For the pharmaceutical and medicinal activity of Schiff bases, see: Dao et al. (2000); Sriram et al. (2006); Karthikeyan et al. (2006). For Schiff base coordination chemistry, see: Ali et al. (2008); Kargar et al. (2009); Yeap et al. (2009). For related structures, see: Fun et al. (2009); Nadeem et al. (2009); Eltayeb et al. (2008). For reference structural data, see: Allen et al. (1987).

Experimental top

2-Hydroxy-1-naphthylaldehyde (0.1 mmol, 17.2 mg) and N-phenylethane-1,2-diamine (0.1 mmol, 13.6 mg) were refluxed in a 30 ml methanol solution for 30 min to give a clear orange solution. Yellow block-shaped single crystals of the compound were formed by slow evaporation of the solvent over several days at room temperature.

Refinement top

In the absence of significant anomalous dispersion effects, 1421 Freidel pairs were merged. H1 was located from a difference Fourier map and refined isotropically, with the N–H distance restrained to 0.90 (1)Å, and with Uiso restrained to 0.08Å2. Other H atoms were constrained to ideal geometries, with d(C–H) = 0.93–0.97Å, d(N–H) = 0.86Å, and with Uiso(H) = 1.2Ueq(C,N).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) with 30% probability ellipsoids. The intramolecular N–H···O hydrogen bond is shown as a dashed line.
[Figure 2] Fig. 2. Molecular packing of (I) with hydrogen bonds drawn as dashed lines.
1-[(2-Anilinoethyl)iminiomethyl]-2-naphtholate top
Crystal data top
C19H18N2OF(000) = 616
Mr = 290.35Dx = 1.237 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 1258 reflections
a = 27.511 (3) Åθ = 2.5–24.5°
b = 6.845 (2) ŵ = 0.08 mm1
c = 8.543 (2) ÅT = 298 K
β = 104.263 (2)°Block, yellow
V = 1559.2 (6) Å30.23 × 0.21 × 0.18 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
1753 independent reflections
Radiation source: fine-focus sealed tube1312 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
ω scansθmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 3135
Tmin = 0.982, Tmax = 0.986k = 68
4485 measured reflectionsl = 1111
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0531P)2 + 0.1092P]
where P = (Fo2 + 2Fc2)/3
1753 reflections(Δ/σ)max < 0.001
202 parametersΔρmax = 0.18 e Å3
3 restraintsΔρmin = 0.18 e Å3
Crystal data top
C19H18N2OV = 1559.2 (6) Å3
Mr = 290.35Z = 4
Monoclinic, CcMo Kα radiation
a = 27.511 (3) ŵ = 0.08 mm1
b = 6.845 (2) ÅT = 298 K
c = 8.543 (2) Å0.23 × 0.21 × 0.18 mm
β = 104.263 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
1753 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1312 reflections with I > 2σ(I)
Tmin = 0.982, Tmax = 0.986Rint = 0.021
4485 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0383 restraints
wR(F2) = 0.105H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.18 e Å3
1753 reflectionsΔρmin = 0.18 e Å3
202 parameters
Special details top

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 > 2sigma(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
O10.52924 (7)0.9086 (3)0.4162 (2)0.0576 (5)
N10.53391 (8)0.5581 (3)0.5306 (3)0.0497 (5)
N20.46277 (8)0.2671 (3)0.3271 (3)0.0522 (6)
H20.49120.22020.32070.063*
C10.60256 (9)0.7135 (4)0.4543 (3)0.0465 (6)
C20.57425 (10)0.8886 (4)0.4038 (3)0.0491 (6)
C30.59731 (11)1.0404 (4)0.3330 (4)0.0608 (7)
H30.57931.15370.29740.073*
C40.64475 (12)1.0231 (5)0.3167 (4)0.0658 (8)
H40.65831.12470.26890.079*
C50.67481 (11)0.8544 (5)0.3702 (3)0.0583 (7)
C60.72446 (13)0.8429 (6)0.3537 (5)0.0791 (10)
H60.73740.94330.30270.095*
C70.75394 (13)0.6840 (7)0.4128 (5)0.0908 (12)
H70.78680.67750.40310.109*
C80.73446 (14)0.5358 (7)0.4859 (6)0.0953 (13)
H80.75460.42940.52690.114*
C90.68608 (12)0.5403 (5)0.5000 (5)0.0748 (9)
H90.67380.43600.54870.090*
C100.65441 (10)0.6995 (4)0.4422 (3)0.0541 (7)
C110.57962 (10)0.5575 (4)0.5134 (3)0.0490 (6)
H110.59850.44450.54270.059*
C120.50873 (11)0.3947 (4)0.5875 (4)0.0568 (7)
H12A0.50460.42370.69450.068*
H12B0.52930.27840.59480.068*
C130.45822 (10)0.3570 (4)0.4749 (4)0.0540 (7)
H13A0.43890.27240.52780.065*
H13B0.44030.47960.45040.065*
C140.42170 (10)0.2552 (4)0.1944 (3)0.0477 (6)
C150.42493 (12)0.1449 (4)0.0608 (4)0.0590 (7)
H150.45420.07590.06270.071*
C160.38583 (14)0.1359 (4)0.0735 (4)0.0689 (9)
H160.38900.06050.16090.083*
C170.34208 (13)0.2356 (5)0.0821 (5)0.0732 (9)
H170.31570.22910.17420.088*
C180.33809 (12)0.3459 (5)0.0492 (4)0.0687 (8)
H180.30880.41540.04540.082*
C190.37702 (11)0.3545 (4)0.1862 (4)0.0579 (7)
H190.37340.42760.27430.070*
H10.5170 (12)0.671 (3)0.501 (4)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0519 (11)0.0450 (10)0.0754 (13)0.0099 (8)0.0146 (9)0.0058 (9)
N10.0534 (14)0.0385 (12)0.0542 (13)0.0029 (9)0.0075 (11)0.0009 (9)
N20.0450 (12)0.0432 (12)0.0711 (15)0.0038 (9)0.0196 (11)0.0043 (10)
C10.0464 (14)0.0426 (13)0.0468 (13)0.0018 (11)0.0048 (11)0.0035 (11)
C20.0530 (16)0.0412 (14)0.0482 (15)0.0029 (11)0.0032 (12)0.0041 (11)
C30.0627 (18)0.0502 (17)0.0656 (19)0.0018 (13)0.0084 (15)0.0088 (14)
C40.068 (2)0.0579 (18)0.0687 (19)0.0112 (14)0.0112 (16)0.0064 (15)
C50.0512 (15)0.064 (2)0.0569 (16)0.0055 (13)0.0081 (13)0.0087 (13)
C60.058 (2)0.092 (3)0.088 (2)0.0136 (18)0.0210 (18)0.009 (2)
C70.054 (2)0.107 (3)0.112 (3)0.005 (2)0.021 (2)0.014 (3)
C80.063 (2)0.087 (3)0.136 (4)0.025 (2)0.024 (2)0.004 (3)
C90.0580 (19)0.067 (2)0.098 (2)0.0130 (15)0.0163 (18)0.0022 (19)
C100.0495 (15)0.0532 (16)0.0548 (16)0.0020 (12)0.0039 (12)0.0087 (12)
C110.0533 (16)0.0392 (14)0.0500 (14)0.0088 (11)0.0041 (11)0.0025 (11)
C120.0704 (18)0.0447 (14)0.0568 (16)0.0015 (13)0.0184 (14)0.0058 (13)
C130.0594 (16)0.0397 (14)0.0665 (17)0.0028 (12)0.0226 (14)0.0025 (12)
C140.0474 (15)0.0345 (12)0.0659 (17)0.0024 (10)0.0230 (14)0.0004 (11)
C150.0647 (17)0.0372 (13)0.081 (2)0.0035 (12)0.0301 (16)0.0078 (13)
C160.086 (2)0.0496 (18)0.074 (2)0.0129 (17)0.0246 (19)0.0135 (15)
C170.074 (2)0.0609 (19)0.079 (2)0.0137 (17)0.0080 (17)0.0017 (17)
C180.0557 (18)0.0620 (19)0.087 (2)0.0049 (15)0.0152 (17)0.0037 (17)
C190.0548 (16)0.0503 (17)0.0725 (19)0.0072 (12)0.0228 (14)0.0027 (13)
Geometric parameters (Å, º) top
O1—C21.276 (3)C8—C91.366 (5)
N1—C111.302 (3)C8—H80.9300
N1—C121.460 (3)C9—C101.407 (4)
N1—H10.907 (10)C9—H90.9300
N2—C141.392 (3)C11—H110.9300
N2—C131.437 (3)C12—C131.505 (4)
N2—H20.8600C12—H12A0.9700
C1—C111.397 (4)C12—H12B0.9700
C1—C21.436 (4)C13—H13A0.9700
C1—C101.459 (4)C13—H13B0.9700
C2—C31.427 (4)C14—C151.389 (4)
C3—C41.351 (4)C14—C191.391 (4)
C3—H30.9300C15—C161.367 (5)
C4—C51.428 (5)C15—H150.9300
C4—H40.9300C16—C171.370 (5)
C5—C61.409 (4)C16—H160.9300
C5—C101.410 (4)C17—C181.379 (5)
C6—C71.376 (6)C17—H170.9300
C6—H60.9300C18—C191.379 (4)
C7—C81.368 (6)C18—H180.9300
C7—H70.9300C19—H190.9300
C11—N1—C12125.9 (2)C5—C10—C1118.9 (2)
C11—N1—H1114 (2)N1—C11—C1125.0 (2)
C12—N1—H1120 (2)N1—C11—H11117.5
C14—N2—C13120.8 (2)C1—C11—H11117.5
C14—N2—H2119.6N1—C12—C13111.0 (2)
C13—N2—H2119.6N1—C12—H12A109.4
C11—C1—C2119.1 (2)C13—C12—H12A109.4
C11—C1—C10120.8 (2)N1—C12—H12B109.4
C2—C1—C10120.1 (2)C13—C12—H12B109.4
O1—C2—C3119.9 (2)H12A—C12—H12B108.0
O1—C2—C1122.0 (2)N2—C13—C12111.6 (2)
C3—C2—C1118.0 (2)N2—C13—H13A109.3
C4—C3—C2121.4 (3)C12—C13—H13A109.3
C4—C3—H3119.3N2—C13—H13B109.3
C2—C3—H3119.3C12—C13—H13B109.3
C3—C4—C5122.4 (3)H13A—C13—H13B108.0
C3—C4—H4118.8C15—C14—C19117.3 (3)
C5—C4—H4118.8C15—C14—N2119.9 (2)
C6—C5—C10120.1 (3)C19—C14—N2122.8 (2)
C6—C5—C4120.8 (3)C16—C15—C14121.1 (3)
C10—C5—C4119.1 (3)C16—C15—H15119.4
C7—C6—C5120.4 (4)C14—C15—H15119.4
C7—C6—H6119.8C15—C16—C17121.5 (3)
C5—C6—H6119.8C15—C16—H16119.3
C8—C7—C6119.5 (3)C17—C16—H16119.3
C8—C7—H7120.3C16—C17—C18118.3 (3)
C6—C7—H7120.3C16—C17—H17120.9
C9—C8—C7121.5 (4)C18—C17—H17120.9
C9—C8—H8119.2C17—C18—C19120.8 (3)
C7—C8—H8119.2C17—C18—H18119.6
C8—C9—C10121.3 (4)C19—C18—H18119.6
C8—C9—H9119.4C18—C19—C14120.9 (3)
C10—C9—H9119.4C18—C19—H19119.5
C9—C10—C5117.2 (3)C14—C19—H19119.5
C9—C10—C1123.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.91 (1)1.84 (3)2.582 (3)137 (3)
N2—H2···O1i0.862.433.043 (3)129
Symmetry code: (i) x, y1, z.

Experimental details

Crystal data
Chemical formulaC19H18N2O
Mr290.35
Crystal system, space groupMonoclinic, Cc
Temperature (K)298
a, b, c (Å)27.511 (3), 6.845 (2), 8.543 (2)
β (°) 104.263 (2)
V3)1559.2 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.23 × 0.21 × 0.18
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.982, 0.986
No. of measured, independent and
observed [I > 2σ(I)] reflections
4485, 1753, 1312
Rint0.021
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.105, 1.06
No. of reflections1753
No. of parameters202
No. of restraints3
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.18, 0.18

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.907 (10)1.84 (3)2.582 (3)137 (3)
N2—H2···O1i0.862.433.043 (3)129.1
Symmetry code: (i) x, y1, z.
 

References

First citationAli, H. M., Mohamed Mustafa, M. I., Rizal, M. R. & Ng, S. W. (2008). Acta Cryst. E64, m718–m719.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
First citationBruker (2002). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationDao, V.-T., Gaspard, C., Mayer, M., Werner, G. H., Nguyen, S. N. & Michelot, R. J. (2000). Eur. J. Med. Chem. 35, 805–813.  Web of Science CrossRef PubMed CAS Google Scholar
First citationEltayeb, N. E., Teoh, S. G., Chantrapromma, S., Fun, H.-K. & Adnan, R. (2008). Acta Cryst. E64, o576–o577.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
First citationFun, H.-K., Kia, R., Vijesh, A. M. & Isloor, A. M. (2009). Acta Cryst. E65, o349–o350.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
First citationKargar, H., Jamshidvand, A., Fun, H.-K. & Kia, R. (2009). Acta Cryst. E65, m403–m404.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
First citationKarthikeyan, M. S., Prasad, D. J., Poojary, B., Bhat, K. S., Holla, B. S. & Kumari, N. S. (2006). Bioorg. Med. Chem. 14, 7482–7489.  Web of Science CrossRef PubMed CAS Google Scholar
First citationNadeem, S., Shah, M. R. & VanDerveer, D. (2009). Acta Cryst. E65, o897.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSriram, D., Yogeeswari, P., Myneedu, N. S. & Saraswat, V. (2006). Bioorg. Med. Chem. Lett. 16, 2127–2129.  Web of Science CrossRef PubMed CAS Google Scholar
First citationYeap, C. S., Kia, R., Kargar, H. & Fun, H.-K. (2009). Acta Cryst. E65, m570–m571.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar

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