Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 8| August 2010| Page o1885
https://doi.org/10.1107/S1600536810025183

9-Ethyl-9H-carbazole-3-carbaldehyde

Mao-Sen Yuan,a* Li Zhaob and Ran-rong Zhanga

aCollege of Science, Northwest A&F University, Yangling 712100, Shannxi Province, People's Republic of China, and bHospital of Northwest A&F University, Yangling 712100, Shannxi Province, People's Republic of China
*Correspondence e-mail: yuanms@nwsuaf.edu.cn

(Received 18 June 2010; accepted 27 June 2010; online 3 July 2010)

The title mol­ecule, C15H13NO, approximates a planar conformation except for the alkyl chain (ethyl group) bonded to the N atom with a maximum deviation from the least-squares plane through the 15 planar atoms of 0.120 (2) Å for the O atom. The distance of the formyl O atom from the plane of the carbazole ring is 0.227 (2) Å. The N—C bond lengths in the central ring are significantly different, reflecting the electron-withdrawing properties of the aldehyde group. As a consequence, charge transfer may occur from the carbazole N atom to the substituted benzene ring.

Related literature

For the properties of carbazole derivatives, see: van Dijken et al. (2004[Dijken, A. van, Bastiaansen, J. J. A. M., Kiggen, N. M. M., Langeveld, B. M. W., Rothe, C., Monkman, A., Bach, I., Stössel, P. & Brunner, K. (2004). J. Am. Chem. Soc. 126, 7718-7727.]); Li et al. (2005[Li, J., Liu, D., Li, Y., Lee, C.-S., Kwong, H.-L. & Lee, S. (2005). Chem. Mater. 17, 1208-1212.]). For the X-ray structure of 9-ethyl-3,6-diformyl-9H-carbazole, see: Wang et al. (2008[Wang, J. J., Zhang, X., Zhang, B. Q., Wang, G. & Yu, X. Q. (2008). Acta Cryst. E64, o1293.]) and of 9-ethyl-9H-carbazole, see: Kimura et al. (1985[Kimura, T., Kai, Y., Yasuoka, N. & Kasai, N. (1985). Bull. Chem. Soc. Jpn, 58, 2268-2271.]).

[Scheme 1]

Experimental

Crystal data

  • C15H13NO

  • Mr = 223.26

  • Monoclinic, P 21 /n

  • a = 10.6523 (10) Å

  • b = 8.2312 (6) Å

  • c = 13.8005 (12) Å

  • β = 104.387 (1)°

  • V = 1172.10 (17) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 298 K

  • 0.50 × 0.44 × 0.43 mm
Data collection

  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.961, Tmax = 0.967

  • 5763 measured reflections

  • 2065 independent reflections

  • 1313 reflections with I > 2σ(I)

  • Rint = 0.029
Refinement

  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.116

  • S = 1.05

  • 2065 reflections

  • 155 parameters

  • H-atom parameters constrained

  • Δρmax = 0.13 e Å−3

  • Δρmin = −0.11 e Å−3

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810025183/bh2297sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810025183/bh2297Isup2.hkl

checkCIF report


Comment top

Carbazole is a conjugated unit which has interesting optical and electronic properties. A number of carbazole derivatives have been designed and synthesized to be used as luminescent materials and hole-transporting materials (van Dijken et al., 2004; Li et al., 2005). In the course of exploring new luminescent compounds, we obtained an intermediate compound, 9-ethyl-3-formyl-9H-carbazole (I). Here we report the structure and synthesis of (I).

The molecule (Fig. 1) lies approximately in a plane besides the alkyl chain (ethyl group). There is a minor displacement between the oxygen atom O1 and the plane of the carbazole ring. And the distance from the oxygen atom O1 to the carbazole plane (the least-squares plane defined by all the 13 atoms of the carbazole framework) is 0.227 (2) Å. The remarkable difference of N—C bond lengths is observed in this structure: N1—C1 = 1.372 (3), N1—C12 = 1.391 (3) Å, which is obviously different from that of 9-ethyl-3,6-diformyl-9H-carbazole (Wang et al., 2008) and that of 9-ethyl-9H-carbazole (Kimura et al., 1985). The different N—C bond lengths maybe root from the structural asymmetry. The pull-electron property of aldehyde group induces a charge-transfer from nitrogen atom N1 to the benzene ring which connects with the aldehyde group.

The molecules are packed in P21/n space group, which is the same as for 9-ethyl-3,6-diformyl-9H-carbazole, but different from that of 9-ethyl-9H-carbazole (Pbca). There are no classic hydrogen bonds in this structure. However, the weak intermolecular interaction C11—H11···O1 (symmetry code for O1: x-1, y, z), is helpful to the stabilization of the crystal structure (Fig. 2). This intermolecular hydrogen bond is characterized by the H11···O1 separation of 2.54 Å.

Related literature top

For the properties of carbazole derivatives, see: van Dijken et al. (2004); Li et al. (2005). For the X-ray structure of 9-ethyl-3,6-diformyl-9H-carbazole, see: Wang et al. (2008) and for the X-ray structure of 9-ethyl-9H-carbazole, see: Kimura et al. (1985).

Experimental top

9-Ethyl-9H-carbazole (0.30 g, 1.54 mmol) was dissolved in N,N-dimethylformamide (DMF, 10 ml). After cooling the mixture to 273 K, a DMF solution of POCl3 (0.24 g, 1.60 mmol) was slowly added. After stirring for 10 h., the mixture was poured into ice water and further stirred for 0.5 h. The solution was extracted with chloroform and dried over Na2SO4. After removing the solvent, the crude product was purified by recrystallization from ethanol, affording the title compound, (I) (0.29 g, 85%). Then, compound (I) was dissolved in a mixture of solvents, chloroform and hexane, and colorless block crystals were formed on slow evaporation at room temperature over one week.

Refinement top

All H atoms were placed in geometrically calculated positions and refined using a riding model with C—H = 0.93 Å (for aromatic CH), C—H = 0.97 %A (for CH2 groups), and 0.96 %A (for CH3 groups). Their isotropic displacement parameters were set to 1.2 times (1.5 times for CH3 groups) the equivalent displacement parameter of their parent atoms.

Structure description top

Carbazole is a conjugated unit which has interesting optical and electronic properties. A number of carbazole derivatives have been designed and synthesized to be used as luminescent materials and hole-transporting materials (van Dijken et al., 2004; Li et al., 2005). In the course of exploring new luminescent compounds, we obtained an intermediate compound, 9-ethyl-3-formyl-9H-carbazole (I). Here we report the structure and synthesis of (I).

The molecule (Fig. 1) lies approximately in a plane besides the alkyl chain (ethyl group). There is a minor displacement between the oxygen atom O1 and the plane of the carbazole ring. And the distance from the oxygen atom O1 to the carbazole plane (the least-squares plane defined by all the 13 atoms of the carbazole framework) is 0.227 (2) Å. The remarkable difference of N—C bond lengths is observed in this structure: N1—C1 = 1.372 (3), N1—C12 = 1.391 (3) Å, which is obviously different from that of 9-ethyl-3,6-diformyl-9H-carbazole (Wang et al., 2008) and that of 9-ethyl-9H-carbazole (Kimura et al., 1985). The different N—C bond lengths maybe root from the structural asymmetry. The pull-electron property of aldehyde group induces a charge-transfer from nitrogen atom N1 to the benzene ring which connects with the aldehyde group.

The molecules are packed in P21/n space group, which is the same as for 9-ethyl-3,6-diformyl-9H-carbazole, but different from that of 9-ethyl-9H-carbazole (Pbca). There are no classic hydrogen bonds in this structure. However, the weak intermolecular interaction C11—H11···O1 (symmetry code for O1: x-1, y, z), is helpful to the stabilization of the crystal structure (Fig. 2). This intermolecular hydrogen bond is characterized by the H11···O1 separation of 2.54 Å.

For the properties of carbazole derivatives, see: van Dijken et al. (2004); Li et al. (2005). For the X-ray structure of 9-ethyl-3,6-diformyl-9H-carbazole, see: Wang et al. (2008) and for the X-ray structure of 9-ethyl-9H-carbazole, see: Kimura et al. (1985).

Computing details top

Data collection: APEX2 (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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. A view of the molecular packing of (I) along axis b.
9-Ethyl-9H-carbazole-3-carbaldehyde top
Crystal data top
C15H13NOF(000) = 472
Mr = 223.26Dx = 1.265 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1960 reflections
a = 10.6523 (10) Åθ = 2.8–25.2°
b = 8.2312 (6) ŵ = 0.08 mm−1
c = 13.8005 (12) ÅT = 298 K
β = 104.387 (1)°Block, colorless
V = 1172.10 (17) Å30.50 × 0.44 × 0.43 mm
Z = 4
Data collection top
Bruker APEXII CCD area-detector
diffractometer		2065 independent reflections
Radiation source: fine-focus sealed tube1313 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
φ and ω scansθmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		h = −12→12
Tmin = 0.961, Tmax = 0.967k = −9→5
5763 measured reflectionsl = −16→16
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) = 0.116H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0369P)2 + 0.3721P]
where P = (Fo2 + 2Fc2)/3
2065 reflections(Δ/σ)max < 0.001
155 parametersΔρmax = 0.13 e Å−3
0 restraintsΔρmin = −0.11 e Å−3
0 constraints
Crystal data top
C15H13NOV = 1172.10 (17) Å3
Mr = 223.26Z = 4
Monoclinic, P21/nMo Kα radiation
a = 10.6523 (10) ŵ = 0.08 mm−1
b = 8.2312 (6) ÅT = 298 K
c = 13.8005 (12) Å0.50 × 0.44 × 0.43 mm
β = 104.387 (1)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer		2065 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		1313 reflections with I > 2σ(I)
Tmin = 0.961, Tmax = 0.967Rint = 0.029
5763 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.116H-atom parameters constrained
S = 1.05Δρmax = 0.13 e Å−3
2065 reflectionsΔρmin = −0.11 e Å−3
155 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.23808 (16)0.0604 (2)0.36043 (12)0.0579 (5)
O10.83067 (17)0.1354 (3)0.36513 (14)0.0966 (6)
C10.3591 (2)0.0376 (3)0.34470 (15)0.0518 (5)
C20.3972 (2)−0.0683 (3)0.27949 (16)0.0631 (6)
H20.3382−0.13830.23900.076*
C30.5250 (2)−0.0665 (3)0.27648 (16)0.0626 (6)
H30.5528−0.13820.23400.075*
C40.6142 (2)0.0397 (3)0.33530 (15)0.0545 (6)
C50.5753 (2)0.1450 (3)0.40056 (14)0.0529 (5)
H50.63470.21570.44010.063*
C60.44792 (19)0.1444 (2)0.40663 (13)0.0466 (5)
C70.37450 (19)0.2342 (2)0.46404 (14)0.0489 (5)
C80.4063 (2)0.3526 (3)0.53694 (16)0.0639 (6)
H80.49140.38860.55920.077*
C90.3104 (3)0.4162 (3)0.57591 (18)0.0766 (7)
H90.33040.49730.62420.092*
C100.1842 (3)0.3611 (3)0.54428 (19)0.0773 (7)
H100.12110.40630.57200.093*
C110.1490 (2)0.2417 (3)0.47318 (17)0.0666 (7)
H110.06400.20490.45240.080*
C120.2467 (2)0.1786 (3)0.43386 (15)0.0531 (5)
C130.7479 (2)0.0386 (3)0.32700 (18)0.0709 (7)
H130.7716−0.04390.28900.085*
C140.1223 (2)−0.0304 (3)0.31232 (18)0.0747 (7)
H14A0.1251−0.05610.24430.090*
H14B0.04670.03680.30920.090*
C150.1098 (3)−0.1842 (4)0.3666 (2)0.1012 (10)
H15A0.1832−0.25270.36790.152*
H15B0.0318−0.23950.33290.152*
H15C0.1065−0.15930.43390.152*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0484 (11)0.0677 (12)0.0556 (11)−0.0109 (9)0.0089 (8)−0.0058 (10)
O10.0640 (12)0.1300 (18)0.1015 (14)−0.0201 (12)0.0310 (10)0.0030 (13)
C10.0529 (13)0.0550 (13)0.0474 (12)−0.0049 (10)0.0122 (10)0.0044 (10)
C20.0631 (15)0.0672 (16)0.0590 (14)−0.0122 (12)0.0152 (11)−0.0083 (12)
C30.0731 (17)0.0609 (15)0.0577 (14)0.0011 (12)0.0239 (12)−0.0005 (12)
C40.0584 (14)0.0573 (14)0.0494 (12)−0.0012 (11)0.0169 (10)0.0115 (11)
C50.0529 (13)0.0560 (13)0.0480 (12)−0.0121 (10)0.0093 (10)0.0098 (11)
C60.0495 (12)0.0483 (12)0.0411 (11)−0.0056 (10)0.0093 (9)0.0083 (10)
C70.0567 (13)0.0473 (12)0.0427 (11)−0.0095 (10)0.0123 (9)0.0086 (10)
C80.0803 (17)0.0608 (15)0.0553 (13)−0.0202 (13)0.0257 (12)−0.0002 (12)
C90.109 (2)0.0605 (16)0.0702 (16)−0.0180 (15)0.0410 (15)−0.0074 (13)
C100.095 (2)0.0729 (17)0.0764 (17)0.0029 (16)0.0449 (15)0.0022 (15)
C110.0623 (15)0.0761 (17)0.0652 (14)−0.0018 (13)0.0228 (12)0.0092 (14)
C120.0581 (14)0.0559 (13)0.0454 (11)−0.0020 (11)0.0129 (10)0.0079 (11)
C130.0654 (17)0.0861 (19)0.0677 (16)0.0026 (14)0.0289 (13)0.0157 (14)
C140.0548 (15)0.097 (2)0.0704 (15)−0.0197 (13)0.0114 (12)−0.0166 (15)
C150.108 (2)0.108 (2)0.092 (2)−0.0571 (19)0.0328 (17)−0.0225 (19)
Geometric parameters (Å, º) top
N1—C11.372 (3)C7—C121.398 (3)
N1—C121.391 (3)C8—C91.371 (3)
N1—C141.453 (3)C8—H80.9300
O1—C131.208 (3)C9—C101.382 (3)
C1—C21.384 (3)C9—H90.9300
C1—C61.413 (3)C10—C111.374 (3)
C2—C31.372 (3)C10—H100.9300
C2—H20.9300C11—C121.388 (3)
C3—C41.394 (3)C11—H110.9300
C3—H30.9300C13—H130.9300
C4—C51.385 (3)C14—C151.494 (4)
C4—C131.457 (3)C14—H14A0.9700
C5—C61.380 (3)C14—H14B0.9700
C5—H50.9300C15—H15A0.9600
C6—C71.447 (3)C15—H15B0.9600
C7—C81.381 (3)C15—H15C0.9600
C1—N1—C12108.45 (16)C8—C9—C10120.8 (2)
C1—N1—C14125.50 (19)C8—C9—H9119.6
C12—N1—C14125.96 (19)C10—C9—H9119.6
N1—C1—C2128.9 (2)C11—C10—C9122.1 (2)
N1—C1—C6109.47 (18)C11—C10—H10118.9
C2—C1—C6121.60 (19)C9—C10—H10118.9
C3—C2—C1117.8 (2)C10—C11—C12116.7 (2)
C3—C2—H2121.1C10—C11—H11121.7
C1—C2—H2121.1C12—C11—H11121.7
C2—C3—C4121.8 (2)C11—C12—N1128.8 (2)
C2—C3—H3119.1C11—C12—C7122.0 (2)
C4—C3—H3119.1N1—C12—C7109.22 (18)
C5—C4—C3120.0 (2)O1—C13—C4125.7 (3)
C5—C4—C13120.7 (2)O1—C13—H13117.1
C3—C4—C13119.2 (2)C4—C13—H13117.1
C6—C5—C4119.61 (19)N1—C14—C15112.2 (2)
C6—C5—H5120.2N1—C14—H14A109.2
C4—C5—H5120.2C15—C14—H14A109.2
C5—C6—C1119.12 (19)N1—C14—H14B109.2
C5—C6—C7134.79 (19)C15—C14—H14B109.2
C1—C6—C7106.09 (17)H14A—C14—H14B107.9
C8—C7—C12119.5 (2)C14—C15—H15A109.5
C8—C7—C6133.74 (19)C14—C15—H15B109.5
C12—C7—C6106.76 (18)H15A—C15—H15B109.5
C9—C8—C7118.9 (2)C14—C15—H15C109.5
C9—C8—H8120.6H15A—C15—H15C109.5
C7—C8—H8120.6H15B—C15—H15C109.5
C12—N1—C1—C2179.4 (2)C1—C6—C7—C12−0.3 (2)
C14—N1—C1—C22.6 (3)C12—C7—C8—C9−1.9 (3)
C12—N1—C1—C6−1.4 (2)C6—C7—C8—C9178.8 (2)
C14—N1—C1—C6−178.23 (19)C7—C8—C9—C101.1 (3)
N1—C1—C2—C3179.0 (2)C8—C9—C10—C110.0 (4)
C6—C1—C2—C3−0.1 (3)C9—C10—C11—C12−0.2 (3)
C1—C2—C3—C4−1.2 (3)C10—C11—C12—N1−178.6 (2)
C2—C3—C4—C51.4 (3)C10—C11—C12—C7−0.6 (3)
C2—C3—C4—C13−178.5 (2)C1—N1—C12—C11179.4 (2)
C3—C4—C5—C6−0.2 (3)C14—N1—C12—C11−3.8 (3)
C13—C4—C5—C6179.62 (18)C1—N1—C12—C71.2 (2)
C4—C5—C6—C1−1.0 (3)C14—N1—C12—C7178.0 (2)
C4—C5—C6—C7−179.8 (2)C8—C7—C12—C111.7 (3)
N1—C1—C6—C5−178.10 (17)C6—C7—C12—C11−178.88 (19)
C2—C1—C6—C51.2 (3)C8—C7—C12—N1−179.94 (17)
N1—C1—C6—C71.1 (2)C6—C7—C12—N1−0.5 (2)
C2—C1—C6—C7−179.68 (19)C5—C4—C13—O1−8.4 (3)
C5—C6—C7—C8−2.0 (4)C3—C4—C13—O1171.5 (2)
C1—C6—C7—C8179.0 (2)C1—N1—C14—C1586.1 (3)
C5—C6—C7—C12178.6 (2)C12—N1—C14—C15−90.2 (3)

Experimental details

Crystal data
Chemical formulaC15H13NO
Mr223.26
Crystal system, space groupMonoclinic, P21/n
Temperature (K)298
a, b, c (Å)10.6523 (10), 8.2312 (6), 13.8005 (12)
β (°) 104.387 (1)
V (Å3)1172.10 (17)
Z4
Radiation typeMo Kα
µ (mm−1)0.08
Crystal size (mm)0.50 × 0.44 × 0.43
Data collection
DiffractometerBruker APEXII CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.961, 0.967
No. of measured, independent and
observed [I > 2σ(I)] reflections		5763, 2065, 1313
Rint0.029
(sin θ/λ)max (Å−1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.116, 1.05
No. of reflections2065
No. of parameters155
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.13, −0.11

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top
N1—C11.372 (3)N1—C141.453 (3)
N1—C121.391 (3)O1—C131.208 (3)
C1—N1—C12108.45 (16)C12—N1—C14125.96 (19)
C1—N1—C14125.50 (19)
 

Acknowledgements

This work was supported by the PhD Programs Foundation of the Ministry of Education of China (No. 20090204120033).

References

First citationBruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationDijken, A. van, Bastiaansen, J. J. A. M., Kiggen, N. M. M., Langeveld, B. M. W., Rothe, C., Monkman, A., Bach, I., Stössel, P. & Brunner, K. (2004). J. Am. Chem. Soc. 126, 7718–7727.  Web of Science PubMed Google Scholar
 First citationKimura, T., Kai, Y., Yasuoka, N. & Kasai, N. (1985). Bull. Chem. Soc. Jpn, 58, 2268–2271.  CrossRef CAS Web of Science Google Scholar
 First citationLi, J., Liu, D., Li, Y., Lee, C.-S., Kwong, H.-L. & Lee, S. (2005). Chem. Mater. 17, 1208–1212.  Web of Science CrossRef CAS Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWang, J. J., Zhang, X., Zhang, B. Q., Wang, G. & Yu, X. Q. (2008). Acta Cryst. E64, o1293.  Web of Science CSD CrossRef 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
Volume 66| Part 8| August 2010| Page o1885
https://doi.org/10.1107/S1600536810025183
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS