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10-Hydr­­oxy-2-aza­penta­cyclo­[10.8.0.02,10.04,9.015,20]icosa-1(12),4(9),5,7,13,15(20),16,18-octa­ene-3,11-dione

aDepartment of Chemistry, Islamic Azad University, Yazd Branch, Yazd, Iran, and bDepartment of Chemistry, Shahid Beheshti University, G. C., Evin, Tehran 1983963113, Iran
*Correspondence e-mail: sa_hashemian@yahoo.com

(Received 8 February 2011; accepted 13 February 2011; online 23 February 2011)

In the title compound, C19H11NO3, the isoindolinone ring system is approximately planar with a maximum atomic deviation of 0.071 (1) Å and the five-membered ring of the dihydro­benzo[g]indol-3-one unit assumes an envelope conformation. The naphthalene ring system makes a dihedral angle of 39.47 (4)° with the mean plane of the isoindolinone system. Inter­molecular O—H⋯O and C—H⋯O hydrogen bonding helps to stabilize the crystal structure.

Related literature

For applications of naphthyl­amines, see Valenti et al. (2006[Valenti, L. E., De Pauli, C. P. & Giacomelli, C. E. (2006). J. Inorg. Biochem. 100, 192-200.]); Black et al. (1994[Black, D. S. C., Bowyer, M. C., Condie, G. C., Craig, D. C. & Kumar, N. (1994). Tetrahedron, 50, 10983-10994.]).

[Scheme 1]

Experimental

Crystal data
  • C19H11NO3

  • Mr = 301.29

  • Triclinic, [P \overline 1]

  • a = 7.3250 (11) Å

  • b = 9.7916 (16) Å

  • c = 10.4532 (17) Å

  • α = 70.401 (13)°

  • β = 82.503 (13)°

  • γ = 75.862 (12)°

  • V = 683.94 (19) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 298 K

  • 0.40 × 0.30 × 0.29 mm

Data collection
  • Stoe IPDS II diffractometer

  • 7737 measured reflections

  • 3627 independent reflections

  • 3161 reflections with I > 2σ(I)

  • Rint = 0.040

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.136

  • S = 1.13

  • 3627 reflections

  • 212 parameters

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

  • Δρmax = 0.29 e Å−3

  • Δρmin = −0.22 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2—H2⋯O1i 0.96 (2) 1.85 (2) 2.7978 (15) 172.2 (17)
C6—H6⋯O3ii 0.93 2.52 3.1609 (18) 126
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y+2, -z.

Data collection: X-RED32 (Stoe & Cie, 2005[Stoe & Cie (2005). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA (Stoe & Cie, 2005[Stoe & Cie (2005). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); data reduction: X-AREA; 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, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information


Comment top

Naphthylamine is an aromatic amine which can be obtained from nitronaphthalene. Naphthylamines are used in the manufacture of dyes, condensation colors, and rubber and in the synthesis of a large number of chemical (Black et al. 1994; Valenti et al. 2006). Ninhydrin (2,2-dihydroxyindane-1,3-dione) is a chemical used to detect ammonia or primary and secondary amines. The carbon atom of a carbonyl bears a partial positive charge enhanced by neighboring electron withdrawing groups like carbonyl itself. So the central carbon of a 1,2,3-tricarbonyl compound is much more electrophilic than one in a simple ketone. Thus indane-1,2,3-trione reacts readily with nucleophiles, including water. Whereas for most carbonyl compounds, a carbonyl form is more stable than a product of water addition (hydrate), ninhydrin forms a stable hydrate of the central carbon because of the destabilizing effect of the adjacent carbonyl groups.

We report here the crystal structure of 7-hydroxy-7-aH-benzo[g] isoindolino[1,2-α]indole-7,10-dione. The title compound was prepared by the reaction of α-naphthylamine and ninhydrine in molar ratio of 1: 1 in acetone. The structure of title complex is shown in Fig. 1. There are intermolecular hydrogen bondings between O—H···O and C—H···O which play important role in the stabilization of crystalline network (Table 1 & Fig. 2).

Related literature top

For applications of naphthylamines, see Valenti et al. (2006); Black et al. (1994).

Experimental top

The title compound was prepared by the reaction of α- naphthylamine and ninhydrine in molar ratio of 1: 1 in acetone. The mixture was stirred for about 2 h at room temperature. The resulting solution was kept in air. After slow evaporation, single crystals of the title compound suitable for an X-ray diffraction study formed at the bottom of the vessel after 2 weeks (m.p. 138 °C).

Refinement top

Hydroxyl H atom was found in a difference Fourier map and refined isotropically. Other H atoms were positioned geometrically and refined as riding atoms with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: X-RED32 (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-AREA (Stoe & Cie, 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, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at 30% probability level.
[Figure 2] Fig. 2. The packing diagram of the title compound. The intermolecular O—H···O and C—H···O hydrogen bonds are shown as blue dashed lines.
10-Hydroxy-2-azapentacyclo[10.8.0.02,10.04,9.015,20]icosa- 1(12),4(9),5,7,13,15 (20),16,18-octaene-3,11-dione top
Crystal data top
C19H11NO3Z = 2
Mr = 301.29F(000) = 312
Triclinic, P1Dx = 1.463 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.3250 (11) ÅCell parameters from 1011 reflections
b = 9.7916 (16) Åθ = 2.3–25.0°
c = 10.4532 (17) ŵ = 0.10 mm1
α = 70.401 (13)°T = 298 K
β = 82.503 (13)°Block, colorless
γ = 75.862 (12)°0.40 × 0.30 × 0.29 mm
V = 683.94 (19) Å3
Data collection top
Stoe IPDS II
diffractometer
3161 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.040
Graphite monochromatorθmax = 29.3°, θmin = 2.3°
rotation method scansh = 1010
7737 measured reflectionsk = 1313
3627 independent reflectionsl = 1414
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136H atoms treated by a mixture of independent and constrained refinement
S = 1.13 w = 1/[σ2(Fo2) + (0.072P)2 + 0.1037P]
where P = (Fo2 + 2Fc2)/3
3627 reflections(Δ/σ)max < 0.001
212 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.22 e Å3
Crystal data top
C19H11NO3γ = 75.862 (12)°
Mr = 301.29V = 683.94 (19) Å3
Triclinic, P1Z = 2
a = 7.3250 (11) ÅMo Kα radiation
b = 9.7916 (16) ŵ = 0.10 mm1
c = 10.4532 (17) ÅT = 298 K
α = 70.401 (13)°0.40 × 0.30 × 0.29 mm
β = 82.503 (13)°
Data collection top
Stoe IPDS II
diffractometer
3161 reflections with I > 2σ(I)
7737 measured reflectionsRint = 0.040
3627 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.136H atoms treated by a mixture of independent and constrained refinement
S = 1.13Δρmax = 0.29 e Å3
3627 reflectionsΔρmin = 0.22 e Å3
212 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
C10.60706 (15)0.62937 (12)0.49240 (11)0.0298 (2)
C20.69780 (16)0.61664 (13)0.36032 (12)0.0324 (2)
C30.87442 (18)0.53663 (16)0.33404 (14)0.0410 (3)
H30.94880.47110.40420.049*
C40.9358 (2)0.55825 (19)0.19890 (16)0.0494 (3)
H41.05400.50650.17790.059*
C50.8237 (2)0.65604 (19)0.09393 (15)0.0502 (3)
H50.86940.66970.00420.060*
C60.6452 (2)0.73333 (16)0.12066 (13)0.0425 (3)
H60.56900.79680.05070.051*
C70.58481 (16)0.71222 (13)0.25611 (12)0.0332 (2)
C80.40104 (16)0.77784 (12)0.31604 (11)0.0318 (2)
C90.33814 (17)0.94765 (13)0.28511 (13)0.0374 (3)
C100.29102 (17)0.97079 (13)0.41761 (13)0.0358 (3)
C110.19816 (19)1.10289 (14)0.44465 (16)0.0441 (3)
H110.16401.19090.37420.053*
C120.15988 (19)1.09807 (16)0.57670 (17)0.0469 (3)
H120.09811.18430.59630.056*
C130.21185 (17)0.96457 (16)0.68549 (15)0.0413 (3)
C140.1701 (2)0.9614 (2)0.82289 (17)0.0541 (4)
H140.11021.04850.84150.065*
C150.2156 (2)0.8347 (2)0.92698 (17)0.0596 (4)
H150.18900.83591.01610.071*
C160.3028 (2)0.7010 (2)0.90168 (15)0.0545 (4)
H160.33060.61400.97420.065*
C170.34726 (19)0.69747 (16)0.77121 (13)0.0422 (3)
H170.40510.60820.75580.051*
C180.30558 (16)0.82910 (14)0.65996 (12)0.0344 (2)
C190.34334 (15)0.83897 (12)0.52100 (12)0.0310 (2)
O10.67384 (13)0.57343 (10)0.60386 (9)0.0374 (2)
O20.24447 (12)0.73626 (10)0.28658 (9)0.0376 (2)
H20.268 (3)0.630 (2)0.317 (2)0.066 (6)*
O30.32112 (19)1.03639 (12)0.17284 (11)0.0592 (3)
N10.43075 (13)0.72309 (10)0.46469 (9)0.0303 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0310 (5)0.0265 (5)0.0314 (5)0.0044 (4)0.0037 (4)0.0091 (4)
C20.0318 (5)0.0332 (5)0.0334 (5)0.0057 (4)0.0021 (4)0.0128 (4)
C30.0329 (6)0.0468 (7)0.0462 (7)0.0022 (5)0.0040 (5)0.0221 (6)
C40.0366 (6)0.0628 (9)0.0545 (8)0.0073 (6)0.0071 (6)0.0317 (7)
C50.0490 (8)0.0656 (9)0.0402 (7)0.0176 (7)0.0120 (6)0.0237 (7)
C60.0460 (7)0.0487 (7)0.0309 (6)0.0114 (5)0.0016 (5)0.0106 (5)
C70.0339 (5)0.0342 (5)0.0308 (5)0.0075 (4)0.0004 (4)0.0096 (4)
C80.0328 (5)0.0321 (5)0.0268 (5)0.0041 (4)0.0038 (4)0.0057 (4)
C90.0367 (6)0.0319 (5)0.0370 (6)0.0045 (4)0.0026 (4)0.0040 (4)
C100.0323 (5)0.0302 (5)0.0430 (6)0.0053 (4)0.0014 (4)0.0104 (5)
C110.0384 (6)0.0293 (6)0.0628 (8)0.0041 (5)0.0020 (6)0.0146 (5)
C120.0378 (6)0.0398 (7)0.0697 (9)0.0068 (5)0.0044 (6)0.0297 (7)
C130.0310 (5)0.0490 (7)0.0540 (7)0.0105 (5)0.0038 (5)0.0301 (6)
C140.0438 (7)0.0725 (10)0.0611 (9)0.0126 (7)0.0084 (6)0.0447 (9)
C150.0510 (8)0.0929 (13)0.0467 (8)0.0148 (8)0.0065 (6)0.0413 (9)
C160.0540 (8)0.0735 (10)0.0354 (7)0.0126 (7)0.0017 (6)0.0188 (7)
C170.0428 (7)0.0495 (7)0.0346 (6)0.0087 (5)0.0009 (5)0.0158 (5)
C180.0290 (5)0.0408 (6)0.0379 (6)0.0088 (4)0.0016 (4)0.0184 (5)
C190.0278 (5)0.0304 (5)0.0353 (5)0.0060 (4)0.0001 (4)0.0119 (4)
O10.0403 (5)0.0356 (4)0.0330 (4)0.0006 (3)0.0097 (3)0.0091 (3)
O20.0338 (4)0.0389 (5)0.0380 (4)0.0049 (3)0.0085 (3)0.0089 (4)
O30.0753 (8)0.0408 (6)0.0421 (5)0.0017 (5)0.0040 (5)0.0047 (4)
N10.0325 (5)0.0292 (4)0.0265 (4)0.0019 (3)0.0028 (3)0.0080 (3)
Geometric parameters (Å, º) top
C1—O11.2192 (14)C10—C191.3826 (16)
C1—N11.3908 (14)C10—C111.4075 (17)
C1—C21.4829 (16)C11—C121.359 (2)
C2—C31.3855 (16)C11—H110.9300
C2—C71.3858 (16)C12—C131.421 (2)
C3—C41.387 (2)C12—H120.9300
C3—H30.9300C13—C141.420 (2)
C4—C51.393 (2)C13—C181.4307 (17)
C4—H40.9300C14—C151.349 (3)
C5—C61.387 (2)C14—H140.9300
C5—H50.9300C15—C161.404 (3)
C6—C71.3885 (17)C15—H150.9300
C6—H60.9300C16—C171.3704 (18)
C7—C81.4983 (16)C16—H160.9300
C8—O21.4071 (14)C17—C181.4148 (19)
C8—N11.4905 (14)C17—H170.9300
C8—C91.5445 (16)C18—C191.4177 (16)
C9—O31.2037 (16)C19—N11.4278 (14)
C9—C101.4616 (18)O2—H20.96 (2)
O1—C1—N1125.83 (10)C11—C10—C9127.75 (12)
O1—C1—C2127.52 (10)C12—C11—C10118.08 (13)
N1—C1—C2106.62 (9)C12—C11—H11121.0
C3—C2—C7121.55 (11)C10—C11—H11121.0
C3—C2—C1128.81 (11)C11—C12—C13121.64 (12)
C7—C2—C1109.36 (10)C11—C12—H12119.2
C2—C3—C4117.33 (12)C13—C12—H12119.2
C2—C3—H3121.3C14—C13—C12120.91 (13)
C4—C3—H3121.3C14—C13—C18118.03 (14)
C3—C4—C5121.23 (13)C12—C13—C18121.06 (12)
C3—C4—H4119.4C15—C14—C13121.45 (14)
C5—C4—H4119.4C15—C14—H14119.3
C6—C5—C4121.25 (12)C13—C14—H14119.3
C6—C5—H5119.4C14—C15—C16120.45 (14)
C4—C5—H5119.4C14—C15—H15119.8
C5—C6—C7117.34 (13)C16—C15—H15119.8
C5—C6—H6121.3C17—C16—C15120.69 (16)
C7—C6—H6121.3C17—C16—H16119.7
C2—C7—C6121.28 (11)C15—C16—H16119.7
C2—C7—C8109.15 (10)C16—C17—C18120.21 (14)
C6—C7—C8129.57 (11)C16—C17—H17119.9
O2—C8—N1111.82 (9)C18—C17—H17119.9
O2—C8—C7113.83 (9)C17—C18—C19125.32 (11)
N1—C8—C7103.29 (9)C17—C18—C13119.13 (12)
O2—C8—C9104.10 (9)C19—C18—C13115.52 (12)
N1—C8—C9103.13 (9)C10—C19—C18121.92 (11)
C7—C8—C9120.25 (10)C10—C19—N1109.84 (10)
O3—C9—C10129.58 (12)C18—C19—N1128.21 (10)
O3—C9—C8124.77 (12)C8—O2—H2107.6 (12)
C10—C9—C8105.45 (9)C1—N1—C19126.89 (9)
C19—C10—C11121.77 (12)C1—N1—C8111.06 (9)
C19—C10—C9110.43 (10)C19—N1—C8108.74 (9)
O1—C1—C2—C31.8 (2)C11—C12—C13—C180.5 (2)
N1—C1—C2—C3179.64 (12)C12—C13—C14—C15178.73 (14)
O1—C1—C2—C7172.16 (12)C18—C13—C14—C150.5 (2)
N1—C1—C2—C75.70 (13)C13—C14—C15—C161.3 (2)
C7—C2—C3—C41.3 (2)C14—C15—C16—C171.6 (3)
C1—C2—C3—C4171.95 (12)C15—C16—C17—C180.0 (2)
C2—C3—C4—C50.3 (2)C16—C17—C18—C19179.45 (13)
C3—C4—C5—C61.2 (2)C16—C17—C18—C131.7 (2)
C4—C5—C6—C71.6 (2)C14—C13—C18—C172.00 (18)
C3—C2—C7—C60.90 (19)C12—C13—C18—C17177.24 (12)
C1—C2—C7—C6173.56 (11)C14—C13—C18—C19179.92 (11)
C3—C2—C7—C8177.95 (11)C12—C13—C18—C190.68 (17)
C1—C2—C7—C87.60 (13)C11—C10—C19—C180.37 (18)
C5—C6—C7—C20.6 (2)C9—C10—C19—C18177.05 (10)
C5—C6—C7—C8179.17 (13)C11—C10—C19—N1178.75 (11)
C2—C7—C8—O2115.06 (11)C9—C10—C19—N11.33 (14)
C6—C7—C8—O263.66 (17)C17—C18—C19—C10177.17 (12)
C2—C7—C8—N16.39 (12)C13—C18—C19—C100.61 (17)
C6—C7—C8—N1174.89 (13)C17—C18—C19—N10.9 (2)
C2—C7—C8—C9120.48 (11)C13—C18—C19—N1178.66 (10)
C6—C7—C8—C960.81 (18)O1—C1—N1—C1940.41 (18)
O2—C8—C9—O372.49 (16)C2—C1—N1—C19137.50 (11)
N1—C8—C9—O3170.63 (13)O1—C1—N1—C8176.42 (11)
C7—C8—C9—O356.47 (18)C2—C1—N1—C81.48 (12)
O2—C8—C9—C10102.75 (10)C10—C19—N1—C1125.80 (12)
N1—C8—C9—C1014.13 (12)C18—C19—N1—C155.95 (17)
C7—C8—C9—C10128.29 (11)C10—C19—N1—C811.01 (13)
O3—C9—C10—C19176.69 (14)C18—C19—N1—C8167.23 (11)
C8—C9—C10—C198.38 (13)O2—C8—N1—C1119.96 (10)
O3—C9—C10—C116.1 (2)C7—C8—N1—C12.84 (12)
C8—C9—C10—C11168.84 (12)C9—C8—N1—C1128.76 (10)
C19—C10—C11—C120.18 (19)O2—C8—N1—C1995.95 (11)
C9—C10—C11—C12176.77 (12)C7—C8—N1—C19141.25 (9)
C10—C11—C12—C130.3 (2)C9—C8—N1—C1915.33 (11)
C11—C12—C13—C14179.76 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O1i0.96 (2)1.85 (2)2.7978 (15)172.2 (17)
C6—H6···O3ii0.932.523.1609 (18)126
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y+2, z.

Experimental details

Crystal data
Chemical formulaC19H11NO3
Mr301.29
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)7.3250 (11), 9.7916 (16), 10.4532 (17)
α, β, γ (°)70.401 (13), 82.503 (13), 75.862 (12)
V3)683.94 (19)
Z2
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.40 × 0.30 × 0.29
Data collection
DiffractometerStoe IPDS II
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
7737, 3627, 3161
Rint0.040
(sin θ/λ)max1)0.688
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.136, 1.13
No. of reflections3627
No. of parameters212
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.29, 0.22

Computer programs: X-RED32 (Stoe & Cie, 2005), X-AREA (Stoe & Cie, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O1i0.96 (2)1.85 (2)2.7978 (15)172.2 (17)
C6—H6···O3ii0.932.523.1609 (18)126
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y+2, z.
 

Acknowledgements

We are grateful to the Islamic Azad University, Yazd Branch, for financial support.

References

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