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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 9| September 2010| Page o2358
https://doi.org/10.1107/S1600536810032769

(2E)-1-(2,5-Di­methyl-3-thien­yl)-3-(2-meth­­oxy­phen­yl)prop-2-en-1-one

Abdullah M. Asiri,a,b Salman A. Khanb and M. Nawaz Tahirc*

aThe Center of Excellence for Advanced Materials Research, King Abdul Aziz University, Jeddah 21589, PO Box 80203, Saudi Arabia, bDepartment of Chemistry, Faculty of Science, King Abdul Aziz University, Jeddah 21589, PO Box 80203, Saudi Arabia, and cDepartment of Physics, University of Sargodha, Sargodha, Pakistan
*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 14 August 2010; accepted 14 August 2010; online 21 August 2010)

In the title compound, C16H16O2S, the central propenone group is almost planar (r.m.s. deviation = 0.009 Å) and subtends dihedral angles of 8.55 (8) and 16.22 (8)° to the 2-meth­oxy­phenyl and 2,5-dimethyl­thio­phene residues, respectively. The dihedral angle between the ring systems is 23.47 (5)°. In the crystal, mol­ecules are linked by weak C—H⋯π inter­actions and aromatic π–π stacking [phenyl ring centroid–centroid separation = 3.6418 (11) Å; thio­phene–thio­phene ring separation = 3.8727 (9) Å].

Related literature

For background to chalcone derivatives and related crystal structures, see: Asiri et al. (2010a[Asiri, A. M., Khan, S. A. & Tahir, M. N. (2010a). Acta Cryst. E66, o2099.],b[Asiri, A. M., Khan, S. A. & Tahir, M. N. (2010b). Acta Cryst. E66, o2133.],c[Asiri, A. M., Khan, S. A. & Tahir, M. N. (2010c). Acta Cryst. E66, o2259-o2260.]).

[Scheme 1]

Experimental

Crystal data

  • C16H16O2S

  • Mr = 272.35

  • Monoclinic, C 2/c

  • a = 26.2978 (6) Å

  • b = 7.5018 (2) Å

  • c = 14.7242 (3) Å

  • β = 105.771 (1)°

  • V = 2795.45 (11) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.23 mm−1

  • T = 296 K

  • 0.32 × 0.24 × 0.22 mm
Data collection

  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.937, Tmax = 0.942

  • 10569 measured reflections

  • 2516 independent reflections

  • 2150 reflections with I > 2σ(I)

  • Rint = 0.023
Refinement

  • R[F2 > 2σ(F2)] = 0.036

  • wR(F2) = 0.102

  • S = 1.04

  • 2516 reflections

  • 175 parameters

  • H-atom parameters constrained

  • Δρmax = 0.22 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of C1–C6 ring.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
C7—H7A⋯Cg2i 0.96 2.89 3.768 (2) 153
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 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 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810032769/hb5609sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810032769/hb5609Isup2.hkl

checkCIF report


Comment top

In continuation of our syntheses of various chalcone derivatives containing the 2,5-dimethylthiophen-3-yl fragment (Asiri et al., 2010a,b,c), the title compound (I, Fig. 1) is now reported.

Recently we have reported the crystal structures of (II) i.e., (E)-1-(2,5-dimethyl-3-thienyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one (Asiri et al., 2010a), (III) i.e., (2E)-3-(3,4-dimethoxyphenyl)-1-(2,5-dimethylthiophen-3-yl)prop- 2-en-1-one (Asiri et al., 2010b) and (IV) i.e., (E)-1-(2,5-dimethyl-3-thienyl)-3-(2-hydroxyphenyl)prop-2-en-1-one (Asiri et al., 2010c) which contain the common moiety 2,5-dimethylthiophen-3-yl as in (I).

In (I), the group A (C1—C6/O1/C7) of 2-methoxyphenyl, the central propenone B (C8—C10/O2) and group C (C11—C16/S1) of 2,5-dimethylthiophen-3-yl are planar with r. m. s. deviation of 0.0320, 0.0096 and 0.0103 Å, respectively. The dihedral angle between A/B, A/C and B/C is 8.55 (8), 23.47 (5) and 16.22 (8)°, respectively.

In the crystal, the molecules are linked by C—H···π interaction (Table 1), π···π interactions between the centroids of phenyl rings at a distance of 3.6418 (11) Å [symmetry code: - x, - y, 1 - z] and between the centroids of thiophen rings at a distance of 3.8727 (9) Å [symmetry code: 1/2 - x, 1/2 - y, 1 - z].

Related literature top

For background to chalcone derivatives and related crystal structures, see: Asiri et al. (2010a,b,c).

Experimental top

A solution of 3-acetyl-2,5-dimethythiophene (0.38 g, 2.5 mmol) and 2-methoxybenzaldehyde (0.31 g, 2.5 mmol) in ethanolic solution of NaOH (3.0 g in 10 ml of methanol) was stirred for 16 h at room temperature. The solution was poured into ice cold water of pH = 2 (pH adjusted by HCl). The solid was separated and dissolved in CH2Cl2, washed with saturated solution of NaHCO3 and evaporated to dryness. The residual was recrystallized from methanol/chloroform to affoard light yellow prisms of (I).

Yield: 76%; m.p. 364–365 K.

IR (KBr) \vmax cm-1: 2923 (C—H), 1653 (Cδb=O), 1596 (CδbC),

Refinement top

The H-atoms were positioned geometrically (C–H = 0.93–0.96 Å) and refined as riding with Uiso(H) = xUeq(C), where x = 1.5 for methyl and x = 1.2 for aryl H-atoms.

Structure description top

In continuation of our syntheses of various chalcone derivatives containing the 2,5-dimethylthiophen-3-yl fragment (Asiri et al., 2010a,b,c), the title compound (I, Fig. 1) is now reported.

Recently we have reported the crystal structures of (II) i.e., (E)-1-(2,5-dimethyl-3-thienyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one (Asiri et al., 2010a), (III) i.e., (2E)-3-(3,4-dimethoxyphenyl)-1-(2,5-dimethylthiophen-3-yl)prop- 2-en-1-one (Asiri et al., 2010b) and (IV) i.e., (E)-1-(2,5-dimethyl-3-thienyl)-3-(2-hydroxyphenyl)prop-2-en-1-one (Asiri et al., 2010c) which contain the common moiety 2,5-dimethylthiophen-3-yl as in (I).

In (I), the group A (C1—C6/O1/C7) of 2-methoxyphenyl, the central propenone B (C8—C10/O2) and group C (C11—C16/S1) of 2,5-dimethylthiophen-3-yl are planar with r. m. s. deviation of 0.0320, 0.0096 and 0.0103 Å, respectively. The dihedral angle between A/B, A/C and B/C is 8.55 (8), 23.47 (5) and 16.22 (8)°, respectively.

In the crystal, the molecules are linked by C—H···π interaction (Table 1), π···π interactions between the centroids of phenyl rings at a distance of 3.6418 (11) Å [symmetry code: - x, - y, 1 - z] and between the centroids of thiophen rings at a distance of 3.8727 (9) Å [symmetry code: 1/2 - x, 1/2 - y, 1 - z].

For background to chalcone derivatives and related crystal structures, see: Asiri et al. (2010a,b,c).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. View of (I) with displacement ellipsoids drawn at the 50% probability level. H-atoms are shown as small spheres of arbitrary radius.
(2E)-1-(2,5-Dimethyl-3-thienyl)-3-(2-methoxyphenyl)prop-2-en-1-one top
Crystal data top
C16H16O2SF(000) = 1152
Mr = 272.35Dx = 1.294 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2150 reflections
a = 26.2978 (6) Åθ = 2.8–25.3°
b = 7.5018 (2) ŵ = 0.23 mm−1
c = 14.7242 (3) ÅT = 296 K
β = 105.771 (1)°Prism, yellow
V = 2795.45 (11) Å30.32 × 0.24 × 0.22 mm
Z = 8
Data collection top
Bruker Kappa APEXII CCD
diffractometer		2516 independent reflections
Radiation source: fine-focus sealed tube2150 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
Detector resolution: 8.10 pixels mm-1θmax = 25.3°, θmin = 2.8°
ω scansh = −31→31
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		k = −7→9
Tmin = 0.937, Tmax = 0.942l = −17→17
10569 measured reflections
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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0538P)2 + 1.6392P]
where P = (Fo2 + 2Fc2)/3
2516 reflections(Δ/σ)max < 0.001
175 parametersΔρmax = 0.22 e Å−3
0 restraintsΔρmin = −0.21 e Å−3
Crystal data top
C16H16O2SV = 2795.45 (11) Å3
Mr = 272.35Z = 8
Monoclinic, C2/cMo Kα radiation
a = 26.2978 (6) ŵ = 0.23 mm−1
b = 7.5018 (2) ÅT = 296 K
c = 14.7242 (3) Å0.32 × 0.24 × 0.22 mm
β = 105.771 (1)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer		2516 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		2150 reflections with I > 2σ(I)
Tmin = 0.937, Tmax = 0.942Rint = 0.023
10569 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0360 restraints
wR(F2) = 0.102H-atom parameters constrained
S = 1.04Δρmax = 0.22 e Å−3
2516 reflectionsΔρmin = −0.21 e Å−3
175 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
S10.32353 (2)−0.13828 (7)0.41788 (3)0.0540 (2)
O10.00471 (4)0.29215 (18)0.37470 (8)0.0503 (4)
O20.15841 (5)0.0916 (2)0.30351 (8)0.0647 (5)
C10.06920 (6)0.1719 (2)0.50255 (10)0.0365 (5)
C20.08539 (6)0.1235 (2)0.59749 (11)0.0440 (5)
C30.05254 (7)0.1426 (3)0.65564 (12)0.0496 (6)
C40.00255 (7)0.2114 (3)0.61901 (12)0.0525 (6)
C5−0.01489 (6)0.2624 (3)0.52590 (12)0.0480 (6)
C60.01817 (6)0.2439 (2)0.46717 (10)0.0380 (5)
C7−0.04837 (7)0.3475 (3)0.33193 (13)0.0534 (6)
C80.10209 (6)0.1431 (2)0.43825 (11)0.0396 (5)
C90.15220 (6)0.0947 (2)0.45997 (11)0.0423 (5)
C100.18032 (6)0.0649 (2)0.38731 (11)0.0401 (5)
C110.23532 (6)−0.0001 (2)0.41814 (10)0.0361 (5)
C120.26768 (6)0.0008 (2)0.51346 (11)0.0405 (5)
C130.31632 (6)−0.0681 (2)0.52502 (12)0.0448 (5)
C140.36036 (7)−0.0865 (3)0.61379 (14)0.0630 (7)
C150.26100 (6)−0.0727 (2)0.35754 (11)0.0420 (5)
C160.24191 (8)−0.1065 (3)0.25341 (12)0.0626 (7)
H20.119140.077260.622190.0528*
H30.063980.109530.718800.0595*
H4−0.019810.223470.657900.0630*
H5−0.048680.309160.502380.0576*
H7A−0.056350.450240.364450.0800*
H7B−0.072180.252510.335650.0800*
H7C−0.052270.377030.266960.0800*
H80.085760.160890.374470.0476*
H90.170340.078870.523110.0507*
H120.256110.045340.563330.0486*
H14A0.35089−0.026900.664540.0945*
H14B0.39191−0.033900.604740.0945*
H14C0.36651−0.210510.628950.0945*
H16A0.233320.004810.220700.0938*
H16B0.21104−0.180810.240320.0938*
H16C0.26916−0.165270.232550.0938*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0394 (3)0.0688 (3)0.0580 (3)0.0163 (2)0.0204 (2)0.0052 (2)
O10.0342 (6)0.0757 (9)0.0398 (6)0.0147 (6)0.0081 (5)0.0100 (6)
O20.0438 (7)0.1110 (12)0.0373 (7)0.0210 (7)0.0076 (5)0.0071 (7)
C10.0298 (8)0.0410 (9)0.0385 (8)0.0003 (6)0.0091 (6)−0.0011 (6)
C20.0351 (8)0.0551 (10)0.0394 (9)0.0053 (7)0.0061 (7)0.0009 (7)
C30.0500 (10)0.0637 (12)0.0351 (8)0.0017 (9)0.0117 (7)0.0008 (8)
C40.0452 (10)0.0720 (13)0.0459 (10)0.0016 (9)0.0221 (8)−0.0019 (9)
C50.0322 (8)0.0642 (12)0.0488 (10)0.0059 (8)0.0130 (7)−0.0019 (8)
C60.0321 (8)0.0445 (9)0.0367 (8)0.0014 (7)0.0081 (6)0.0000 (7)
C70.0359 (9)0.0684 (12)0.0490 (10)0.0113 (8)−0.0001 (7)0.0044 (8)
C80.0335 (8)0.0471 (9)0.0378 (8)0.0028 (7)0.0088 (6)0.0026 (7)
C90.0323 (8)0.0566 (10)0.0375 (8)0.0064 (7)0.0089 (6)0.0032 (7)
C100.0336 (8)0.0495 (10)0.0364 (8)0.0030 (7)0.0081 (7)0.0018 (7)
C110.0325 (8)0.0409 (9)0.0363 (8)0.0016 (6)0.0116 (6)0.0026 (6)
C120.0330 (8)0.0507 (10)0.0382 (8)0.0014 (7)0.0102 (6)−0.0011 (7)
C130.0352 (9)0.0502 (10)0.0477 (9)0.0018 (7)0.0091 (7)0.0038 (8)
C140.0393 (10)0.0759 (14)0.0635 (12)0.0070 (9)−0.0038 (9)0.0046 (10)
C150.0401 (9)0.0480 (10)0.0405 (8)0.0059 (7)0.0156 (7)0.0056 (7)
C160.0727 (13)0.0774 (14)0.0416 (10)0.0210 (11)0.0224 (9)−0.0023 (9)
Geometric parameters (Å, º) top
S1—C131.7217 (17)C13—C141.499 (3)
S1—C151.7150 (17)C15—C161.500 (2)
O1—C61.3595 (18)C2—H20.9300
O1—C71.428 (2)C3—H30.9300
O2—C101.2281 (19)C4—H40.9300
C1—C21.394 (2)C5—H50.9300
C1—C61.409 (2)C7—H7A0.9600
C1—C81.462 (2)C7—H7B0.9600
C2—C31.379 (2)C7—H7C0.9600
C3—C41.378 (3)C8—H80.9300
C4—C51.376 (2)C9—H90.9300
C5—C61.390 (2)C12—H120.9300
C8—C91.320 (2)C14—H14A0.9600
C9—C101.474 (2)C14—H14B0.9600
C10—C111.476 (2)C14—H14C0.9600
C11—C121.430 (2)C16—H16A0.9600
C11—C151.370 (2)C16—H16B0.9600
C12—C131.347 (2)C16—H16C0.9600
C13—S1—C1593.33 (8)C4—C3—H3120.00
C6—O1—C7118.44 (13)C3—C4—H4119.00
C2—C1—C6118.12 (14)C5—C4—H4119.00
C2—C1—C8122.53 (14)C4—C5—H5120.00
C6—C1—C8119.29 (13)C6—C5—H5120.00
C1—C2—C3121.56 (15)O1—C7—H7A109.00
C2—C3—C4119.19 (16)O1—C7—H7B109.00
C3—C4—C5121.20 (17)O1—C7—H7C109.00
C4—C5—C6119.77 (16)H7A—C7—H7B109.00
O1—C6—C1115.79 (13)H7A—C7—H7C109.00
O1—C6—C5124.05 (15)H7B—C7—H7C109.00
C1—C6—C5120.16 (14)C1—C8—H8116.00
C1—C8—C9127.69 (15)C9—C8—H8116.00
C8—C9—C10122.07 (15)C8—C9—H9119.00
O2—C10—C9120.91 (15)C10—C9—H9119.00
O2—C10—C11121.05 (15)C11—C12—H12123.00
C9—C10—C11118.03 (13)C13—C12—H12123.00
C10—C11—C12124.91 (14)C13—C14—H14A109.00
C10—C11—C15123.12 (14)C13—C14—H14B109.00
C12—C11—C15111.96 (14)C13—C14—H14C109.00
C11—C12—C13114.43 (15)H14A—C14—H14B109.00
S1—C13—C12109.81 (13)H14A—C14—H14C109.00
S1—C13—C14121.30 (13)H14B—C14—H14C109.00
C12—C13—C14128.89 (16)C15—C16—H16A109.00
S1—C15—C11110.47 (12)C15—C16—H16B109.00
S1—C15—C16119.25 (13)C15—C16—H16C109.00
C11—C15—C16130.24 (16)H16A—C16—H16B109.00
C1—C2—H2119.00H16A—C16—H16C109.00
C3—C2—H2119.00H16B—C16—H16C109.00
C2—C3—H3120.00
C15—S1—C13—C120.47 (13)C4—C5—C6—O1−179.28 (18)
C15—S1—C13—C14−179.28 (15)C4—C5—C6—C10.5 (3)
C13—S1—C15—C11−0.36 (13)C1—C8—C9—C10178.07 (15)
C13—S1—C15—C16−177.99 (14)C8—C9—C10—O23.1 (2)
C7—O1—C6—C1173.19 (15)C8—C9—C10—C11−176.16 (15)
C7—O1—C6—C5−7.0 (2)O2—C10—C11—C12166.02 (16)
C6—C1—C2—C30.9 (2)O2—C10—C11—C15−15.4 (2)
C8—C1—C2—C3−176.26 (16)C9—C10—C11—C12−14.7 (2)
C2—C1—C6—O1178.75 (14)C9—C10—C11—C15163.82 (15)
C2—C1—C6—C5−1.1 (2)C10—C11—C12—C13178.89 (14)
C8—C1—C6—O1−4.0 (2)C15—C11—C12—C130.2 (2)
C8—C1—C6—C5176.16 (16)C10—C11—C15—S1−178.56 (12)
C2—C1—C8—C9−10.4 (3)C10—C11—C15—C16−1.3 (3)
C6—C1—C8—C9172.51 (16)C12—C11—C15—S10.16 (17)
C1—C2—C3—C4−0.1 (3)C12—C11—C15—C16177.45 (17)
C2—C3—C4—C5−0.5 (3)C11—C12—C13—S1−0.46 (18)
C3—C4—C5—C60.3 (3)C11—C12—C13—C14179.26 (17)
Hydrogen-bond geometry (Å, º) top
Cg2 is the centroid of C1–C6 ring.
D—H···AD—HH···AD···AD—H···A
C7—H7A···Cg2i0.962.893.768 (2)153
Symmetry code: (i) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formulaC16H16O2S
Mr272.35
Crystal system, space groupMonoclinic, C2/c
Temperature (K)296
a, b, c (Å)26.2978 (6), 7.5018 (2), 14.7242 (3)
β (°) 105.771 (1)
V (Å3)2795.45 (11)
Z8
Radiation typeMo Kα
µ (mm−1)0.23
Crystal size (mm)0.32 × 0.24 × 0.22
Data collection
DiffractometerBruker Kappa APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.937, 0.942
No. of measured, independent and
observed [I > 2σ(I)] reflections		10569, 2516, 2150
Rint0.023
(sin θ/λ)max (Å−1)0.600
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.102, 1.04
No. of reflections2516
No. of parameters175
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.22, −0.21

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
Cg2 is the centroid of C1–C6 ring.
D—H···AD—HH···AD···AD—H···A
C7—H7A···Cg2i0.962.893.768 (2)153
Symmetry code: (i) −x, −y+1, −z+1.
 

Acknowledgements

The authors would like to thank the Chemistry Department, King Abdul Aziz University, Jeddah, Saudi Arabia, for providing the research facilities and for the financial support of this work via grant No. (3–045/430).

References

First citationAsiri, A. M., Khan, S. A. & Tahir, M. N. (2010a). Acta Cryst. E66, o2099.  Web of Science CSD CrossRef IUCr Journals Google Scholar
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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.

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ISSN: 2056-9890
Volume 66| Part 9| September 2010| Page o2358
https://doi.org/10.1107/S1600536810032769
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