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 64| Part 1| January 2008| Page o151
https://doi.org/10.1107/S1600536807063489

3-Phenyl-1-(pyrrol-2-yl)prop-2-en-1-one

Zhen-Qi Gong,a* Gou-Sheng Liua and Hong-Ying Xiaa

aDepartment of Chemistry, Jiangxi Science and Technology Normal University, Jiangxi 330013, People's Republic of China
*Correspondence e-mail: zhqgong@126.com

(Received 15 November 2007; accepted 26 November 2007; online 6 December 2007)

The title mol­ecule, C13H11NO, is almost flat, the angle between the pyrrole and the phenyl rings being 10.9 (1)°. The atoms of the central C3O unit are coplanar, with a mean deviation from the plane of 0.001 (1) Å. The angles between this plane and the pyrrole and phenyl rings are 3.3 (1) and 8.0 (1)°, respectively. The mol­ecules form centrosymmetric dimers through a pair of N—H⋯O hydrogen bonds with an R22(10) motif.

Related literature

For details of the biological and the pharmaceutical properties of chalcones, see: Chen et al. (1999[Chen, M., Zhai, L., Christensen, S. B., Theander, T. G. & Kharazami, A. (1999). Antimicrob. Agents Chemother. 43, 793-801.]); Dimmock et al. (1999[Dimmock, J. R., Elias, D. W., Beazely, M. A. & Kandepu, N. (1999). Curr. Med. Chem. 6, 1125-1149.]); Go et al. (2005[Go, M. L., Wu, X. & Liu, X.-L. (2005). Curr. Med. Chem. 12, 481-499.]); Lin et al. (2002[Lin, Y. M., Zhou, Y., Flavin, M. T., Zhou, L. M., Nie, W. & Chen, F. C. (2002). Bioorg. Med. Chem. 16, 2795-2802.]); Lunardi et al. (2003[Lunardi, F., Guzhela, M., Rodrigues, A. T., Correa, R., Calixtio, J. B. & Santos, A. R. S. (2003). Antimicrob. Agents Chemother. 47, 1449-1456.]); Opletalova (2000[Opletalova, V. (2000). Ceska Slov. Farm. 49, 278-284.]). For other related literature, see: Gong & Shen (2007[Gong, Z.-Q. & Shen, Y.-L. (2007). Acta Cryst. E63, o3939.]); Kumaran et al. (1996[Kumaran, D., Eswaramoorthy, S., Ponnuswamy, M. N., Raju, K. S. & Nanjundan, S. (1996). Acta Cryst. C52, 2543-2545.]); Shanmuga Sundara Raj et al. (1997[Shanmuga Sundara Raj, S., Ponnuswamy, M. N., Shanmugam, G. & Nanjundan, S. (1997). Acta Cryst. C53, 917-918.], 1998[Shanmuga Sundara Raj, S., Ponnuswamy, M. N., Shanmugam, G. & Nanjundan, S. (1998). Acta Cryst. C54, 541-542.]). For a description of hydrogen-bond motifs, see: Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]).

[Scheme 1]

Experimental

Crystal data

  • C13H11NO

  • Mr = 197.23

  • Monoclinic, C 2/c

  • a = 19.848 (4) Å

  • b = 5.6435 (12) Å

  • c = 19.325 (4) Å

  • β = 101.535 (4)°

  • V = 2120.9 (8) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 293 (2) K

  • 0.34 × 0.13 × 0.11 mm
Data collection

  • Bruker APEX area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.974, Tmax = 0.991

  • 5274 measured reflections

  • 2069 independent reflections

  • 1164 reflections with I > 2σ(I)

  • Rint = 0.040
Refinement

  • R[F2 > 2σ(F2)] = 0.054

  • wR(F2) = 0.137

  • S = 1.00

  • 2069 reflections

  • 136 parameters

  • H-atom parameters constrained

  • Δρmax = 0.13 e Å−3

  • Δρmin = −0.13 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1⋯O1i 0.86 2.02 2.817 (2) 155
C7—H7⋯O1 0.93 2.51 2.835 (3) 101
Symmetry code: (i) -x+1, -y, -z+1.

Data collection: SMART (Bruker, 2002[Bruker (2002). SAINT (Version 6.36A), SMART (Version 5.626) and SHELXTL (Version 6.10). Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SAINT (Version 6.36A), SMART (Version 5.626) and SHELXTL (Version 6.10). Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990[Sheldrick, G. M. (1990). Acta Cryst. A46, 467-473.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXL97. University of Göttingen, Germany.]); molecular graphics: SHELXTL (Bruker, 2002[Bruker (2002). SAINT (Version 6.36A), SMART (Version 5.626) and SHELXTL (Version 6.10). Bruker AXS Inc., Madison, Wisconsin, USA.]); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536807063489/fb2072sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807063489/fb2072Isup2.hkl

checkCIF report


Comment top

Chalcone derivatives possess wide variety of pharmaceutical properties, such as anticancer, antibacterial, antiviral, antiprotozoal, insecticidal and enzyme-inhibitory ones (Dimmock et al., 1999; Go et al., 2005; Opletalova, 2000). Some of the substituted chalcones are also reported to possess antileishmanial (Chen et al., 1999), antitubercular (Lin et al., 2002), trypanocidal (Lunardi et al., 2003) activities. As a part of our ongoing efforts in the chalcone compounds (Gong & Shen, 2007), the title compound is reported here for the first time.

In the title compound, C13H11NO, the bond lengths and angles are usual. The –NH groups are involved as donors to form centrosymmetric dimers with a motif R22(10) through N—H···O hydrogen bonds (Etter et al., 1990) - (Fig. 2). There is a pyrrole-H···π-phenyl-ring interaction as indicate the geometric parameters C2—H2···Centroid(phenyl) (1 - x, y, 3/2 - z) where the distance H···centroid and C2···centroid equal to 2.90 and 3.666 (3) Å, respectively, and the angle C2—H2···Centroid(phenyl) equals to 141° (Spek, 2003).

Related literature top

For details of the biological and the pharmaceutical properties of chalcones, see: Chen et al. (1999); Dimmock et al. (1999); Go et al. (2005); Lin et al. (2002); Lunardi et al. (2003); Opletalova (2000). For other related literature, see: Gong & Shen (2007); Kumaran et al. (1996); Shanmuga Sundara Raj et al. (1997, 1998). For a description of hydrogen-bond motifs, see: Etter et al. (1990).

Experimental top

2-Acetylpyrrole (2.18 g, 20.0 mmol) was added to a solution of benzaldehyde (1.06 g, 10.0 mmol) in methanol (65 ml). Then potassium hydroxide (1.12 g, 20 mmol) and ammonia (25%, 50 ml) were added to the solution and refluxed for 12 h. The resulting solution was cooled and the solvent was evaporated under vacuum to give an orange precipitate which was separated by filtration, washed with iced ethanol (95%) and water to pH = 7. Recrystallization from dichloromethane gave light yellow prism-like crystals with average size of about 1.50x0.35x0.25 mm. Yield: 0.89 g (45%).

Refinement top

All the H atoms could be distinguished in the difference Fourier map. Nevertheless, the H atoms were set into idealized positions and constrained by the riding motion formalism: The C—H and N—H distances were set to 0.93 and 0.86 Å, respectively, while Uiso=1.2Ueq of the pertinent carrier atom.

Structure description top

Chalcone derivatives possess wide variety of pharmaceutical properties, such as anticancer, antibacterial, antiviral, antiprotozoal, insecticidal and enzyme-inhibitory ones (Dimmock et al., 1999; Go et al., 2005; Opletalova, 2000). Some of the substituted chalcones are also reported to possess antileishmanial (Chen et al., 1999), antitubercular (Lin et al., 2002), trypanocidal (Lunardi et al., 2003) activities. As a part of our ongoing efforts in the chalcone compounds (Gong & Shen, 2007), the title compound is reported here for the first time.

In the title compound, C13H11NO, the bond lengths and angles are usual. The –NH groups are involved as donors to form centrosymmetric dimers with a motif R22(10) through N—H···O hydrogen bonds (Etter et al., 1990) - (Fig. 2). There is a pyrrole-H···π-phenyl-ring interaction as indicate the geometric parameters C2—H2···Centroid(phenyl) (1 - x, y, 3/2 - z) where the distance H···centroid and C2···centroid equal to 2.90 and 3.666 (3) Å, respectively, and the angle C2—H2···Centroid(phenyl) equals to 141° (Spek, 2003).

For details of the biological and the pharmaceutical properties of chalcones, see: Chen et al. (1999); Dimmock et al. (1999); Go et al. (2005); Lin et al. (2002); Lunardi et al. (2003); Opletalova (2000). For other related literature, see: Gong & Shen (2007); Kumaran et al. (1996); Shanmuga Sundara Raj et al. (1997, 1998). For a description of hydrogen-bond motifs, see: Etter et al. (1990).

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, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXTL (Bruker, 2002) and PLATON (Spek (2003).

Figures top
[Figure 1] Fig. 1. The title molecule with the displacement ellipsoids shown at the 30% probability level, and with the H atoms shown as spheres of arbitrary radii.
[Figure 2] Fig. 2. A motif showing the N—H···.O hydrogen bonds. The H atoms not involved in hydrogen bonding have been omitted for clarity.
3-Phenyl-1-(pyrrol-2-yl)prop-2-en-1-one top
Crystal data top
C13H11NOF(000) = 832
Mr = 197.23Dx = 1.235 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 642 reflections
a = 19.848 (4) Åθ = 2.7–24.7°
b = 5.6435 (12) ŵ = 0.08 mm−1
c = 19.325 (4) ÅT = 293 K
β = 101.535 (4)°Prism, light yellow
V = 2120.9 (8) Å30.34 × 0.13 × 0.11 mm
Z = 8
Data collection top
Bruker APEX area-detector
diffractometer		2069 independent reflections
Radiation source: fine-focus sealed tube1164 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
φ and ω scansθmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −24→23
Tmin = 0.974, Tmax = 0.991k = −6→6
5274 measured reflectionsl = −14→23
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)] = 0.054Hydrogen site location: difference Fourier map
wR(F2) = 0.137H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0534P)2 + 0.0616P]
where P = (Fo2 + 2Fc2)/3
2069 reflections(Δ/σ)max < 0.001
136 parametersΔρmax = 0.13 e Å−3
0 restraintsΔρmin = −0.13 e Å−3
44 constraints
Crystal data top
C13H11NOV = 2120.9 (8) Å3
Mr = 197.23Z = 8
Monoclinic, C2/cMo Kα radiation
a = 19.848 (4) ŵ = 0.08 mm−1
b = 5.6435 (12) ÅT = 293 K
c = 19.325 (4) Å0.34 × 0.13 × 0.11 mm
β = 101.535 (4)°
Data collection top
Bruker APEX area-detector
diffractometer		2069 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		1164 reflections with I > 2σ(I)
Tmin = 0.974, Tmax = 0.991Rint = 0.040
5274 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0540 restraints
wR(F2) = 0.137H-atom parameters constrained
S = 1.00Δρmax = 0.13 e Å−3
2069 reflectionsΔρmin = −0.13 e Å−3
136 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
O10.54821 (8)0.1673 (3)0.58099 (8)0.0776 (5)
N10.41400 (9)0.2050 (3)0.50060 (9)0.0635 (5)
H10.43490.08470.48740.076*
C10.44232 (11)0.3625 (4)0.55205 (10)0.0547 (6)
C20.39177 (12)0.5253 (4)0.55675 (12)0.0673 (7)
H20.39610.65360.58750.081*
C30.33346 (12)0.4656 (4)0.50787 (13)0.0762 (7)
H30.29160.54560.49970.091*
C40.34890 (12)0.2665 (4)0.47383 (12)0.0724 (7)
H40.31910.18710.43800.087*
C50.51165 (12)0.3362 (4)0.59096 (11)0.0586 (6)
C60.53729 (12)0.5178 (4)0.64459 (11)0.0640 (6)
H60.50830.64270.65030.077*
C70.59949 (12)0.5118 (4)0.68497 (11)0.0609 (6)
H70.62740.38600.67750.073*
C80.62940 (11)0.6813 (4)0.74025 (10)0.0564 (6)
C90.69227 (11)0.6324 (4)0.78395 (11)0.0645 (6)
H90.71590.49530.77670.077*
C100.72018 (13)0.7842 (5)0.83802 (13)0.0733 (7)
H100.76220.74860.86710.088*
C110.68593 (15)0.9879 (5)0.84886 (13)0.0780 (8)
H110.70461.08980.88550.094*
C120.62420 (14)1.0411 (4)0.80554 (13)0.0782 (7)
H120.60111.17940.81280.094*
C130.59620 (13)0.8898 (4)0.75115 (12)0.0699 (7)
H130.55470.92830.72160.084*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0839 (12)0.0726 (11)0.0687 (11)0.0236 (9)−0.0030 (8)−0.0209 (8)
N10.0670 (12)0.0654 (12)0.0563 (11)0.0096 (10)0.0076 (9)−0.0115 (10)
C10.0643 (14)0.0543 (14)0.0453 (12)0.0030 (11)0.0102 (11)−0.0051 (11)
C20.0730 (15)0.0639 (16)0.0651 (15)0.0084 (13)0.0138 (13)−0.0107 (12)
C30.0672 (15)0.0833 (18)0.0767 (17)0.0166 (14)0.0114 (14)−0.0072 (14)
C40.0619 (15)0.0858 (18)0.0661 (15)0.0029 (14)0.0051 (12)−0.0102 (14)
C50.0749 (16)0.0527 (14)0.0486 (13)0.0075 (12)0.0134 (11)−0.0024 (11)
C60.0732 (15)0.0575 (15)0.0609 (14)0.0051 (12)0.0123 (12)−0.0109 (11)
C70.0684 (14)0.0583 (15)0.0579 (14)0.0009 (12)0.0174 (12)−0.0049 (11)
C80.0646 (14)0.0539 (14)0.0521 (13)−0.0081 (12)0.0154 (11)−0.0037 (11)
C90.0660 (15)0.0655 (15)0.0631 (15)−0.0076 (12)0.0157 (12)−0.0018 (12)
C100.0717 (16)0.0802 (18)0.0669 (16)−0.0221 (15)0.0110 (12)−0.0012 (14)
C110.104 (2)0.0711 (19)0.0591 (15)−0.0342 (16)0.0157 (15)−0.0060 (13)
C120.108 (2)0.0550 (15)0.0728 (18)−0.0107 (15)0.0210 (16)−0.0106 (13)
C130.0828 (16)0.0579 (14)0.0672 (16)−0.0021 (13)0.0105 (13)−0.0049 (12)
Geometric parameters (Å, º) top
O1—C51.236 (2)C7—C81.468 (3)
N1—C41.338 (3)C7—H70.9300
N1—C11.368 (2)C8—C131.385 (3)
N1—H10.8600C8—C91.387 (3)
C1—C21.377 (3)C9—C101.379 (3)
C1—C51.438 (3)C9—H90.9300
C2—C31.381 (3)C10—C111.373 (3)
C2—H20.9300C10—H100.9300
C3—C41.367 (3)C11—C121.372 (3)
C3—H30.9300C11—H110.9300
C4—H40.9300C12—C131.382 (3)
C5—C61.474 (3)C12—H120.9300
C6—C71.322 (3)C13—H130.9300
C6—H60.9300
C4—N1—C1109.70 (18)C6—C7—C8127.4 (2)
C4—N1—H1125.2C6—C7—H7116.3
C1—N1—H1125.2C8—C7—H7116.3
N1—C1—C2106.42 (18)C13—C8—C9118.3 (2)
N1—C1—C5121.59 (19)C13—C8—C7121.9 (2)
C2—C1—C5132.0 (2)C9—C8—C7119.8 (2)
C1—C2—C3108.3 (2)C10—C9—C8120.9 (2)
C1—C2—H2125.8C10—C9—H9119.5
C3—C2—H2125.8C8—C9—H9119.5
C4—C3—C2107.0 (2)C11—C10—C9120.0 (2)
C4—C3—H3126.5C11—C10—H10120.0
C2—C3—H3126.5C9—C10—H10120.0
N1—C4—C3108.6 (2)C12—C11—C10119.9 (2)
N1—C4—H4125.7C12—C11—H11120.0
C3—C4—H4125.7C10—C11—H11120.0
O1—C5—C1121.92 (19)C11—C12—C13120.2 (3)
O1—C5—C6121.0 (2)C11—C12—H12119.9
C1—C5—C6117.1 (2)C13—C12—H12119.9
C7—C6—C5123.2 (2)C12—C13—C8120.6 (2)
C7—C6—H6118.4C12—C13—H13119.7
C5—C6—H6118.4C8—C13—H13119.7
C4—N1—C1—C20.4 (2)C1—C5—C6—C7178.6 (2)
C4—N1—C1—C5178.7 (2)C5—C6—C7—C8−179.1 (2)
N1—C1—C2—C3−0.3 (3)C6—C7—C8—C13−7.4 (3)
C5—C1—C2—C3−178.3 (2)C6—C7—C8—C9171.7 (2)
C1—C2—C3—C40.1 (3)C13—C8—C9—C101.6 (3)
C1—N1—C4—C3−0.3 (3)C7—C8—C9—C10−177.45 (19)
C2—C3—C4—N10.2 (3)C8—C9—C10—C11−0.5 (3)
N1—C1—C5—O1−1.8 (3)C9—C10—C11—C12−0.5 (4)
C2—C1—C5—O1175.9 (2)C10—C11—C12—C130.2 (4)
N1—C1—C5—C6179.22 (18)C11—C12—C13—C81.0 (4)
C2—C1—C5—C6−3.0 (4)C9—C8—C13—C12−1.9 (3)
O1—C5—C6—C7−0.4 (3)C7—C8—C13—C12177.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.862.022.817 (2)155
C7—H7···O10.932.512.835 (3)101
Symmetry code: (i) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formulaC13H11NO
Mr197.23
Crystal system, space groupMonoclinic, C2/c
Temperature (K)293
a, b, c (Å)19.848 (4), 5.6435 (12), 19.325 (4)
β (°) 101.535 (4)
V (Å3)2120.9 (8)
Z8
Radiation typeMo Kα
µ (mm−1)0.08
Crystal size (mm)0.34 × 0.13 × 0.11
Data collection
DiffractometerBruker APEX area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.974, 0.991
No. of measured, independent and
observed [I > 2σ(I)] reflections		5274, 2069, 1164
Rint0.040
(sin θ/λ)max (Å−1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.054, 0.137, 1.00
No. of reflections2069
No. of parameters136
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.13, −0.13

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2002) and PLATON (Spek (2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.862.022.817 (2)154.7
C7—H7···O10.932.512.835 (3)100.7
Symmetry code: (i) −x+1, −y, −z+1.
 

Acknowledgements

The authors thank Jiangxi Science and Technology Normal University for the support of this study.

References

First citationBruker (2002). SAINT (Version 6.36A), SMART (Version 5.626) and SHELXTL (Version 6.10). Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationChen, M., Zhai, L., Christensen, S. B., Theander, T. G. & Kharazami, A. (1999). Antimicrob. Agents Chemother. 43, 793–801.  Google Scholar
 First citationDimmock, J. R., Elias, D. W., Beazely, M. A. & Kandepu, N. (1999). Curr. Med. Chem. 6, 1125–1149.  Web of Science PubMed CAS Google Scholar
 First citationEtter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256–262.  CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationGo, M. L., Wu, X. & Liu, X.-L. (2005). Curr. Med. Chem. 12, 481–499.  CrossRef PubMed CAS Google Scholar
 First citationGong, Z.-Q. & Shen, Y.-L. (2007). Acta Cryst. E63, o3939.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationKumaran, D., Eswaramoorthy, S., Ponnuswamy, M. N., Raju, K. S. & Nanjundan, S. (1996). Acta Cryst. C52, 2543–2545.  CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationLin, Y. M., Zhou, Y., Flavin, M. T., Zhou, L. M., Nie, W. & Chen, F. C. (2002). Bioorg. Med. Chem. 16, 2795–2802.  Web of Science CrossRef Google Scholar
 First citationLunardi, F., Guzhela, M., Rodrigues, A. T., Correa, R., Calixtio, J. B. & Santos, A. R. S. (2003). Antimicrob. Agents Chemother. 47, 1449–1456.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationOpletalova, V. (2000). Ceska Slov. Farm. 49, 278–284.  PubMed CAS Google Scholar
 First citationShanmuga Sundara Raj, S., Ponnuswamy, M. N., Shanmugam, G. & Nanjundan, S. (1997). Acta Cryst. C53, 917–918.  CSD CrossRef CAS IUCr Journals Google Scholar
 First citationShanmuga Sundara Raj, S., Ponnuswamy, M. N., Shanmugam, G. & Nanjundan, S. (1998). Acta Cryst. C54, 541–542.  CSD CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (1990). Acta Cryst. A46, 467–473.  CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (1997). SHELXL97. University of Göttingen, Germany.  Google Scholar
 First citationSpek, A. L. (2003). J. Appl. Cryst. 36, 7–13.  Web of Science 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
Volume 64| Part 1| January 2008| Page o151
https://doi.org/10.1107/S1600536807063489
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