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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 2| February 2010| Page o311
https://doi.org/10.1107/S1600536809055615

(E)-5-Meth­­oxy-2-(o-tolyl­imino­meth­yl)phenol

Çiğdem Albayrak,a Başak Koşar,a Arzu Özek,b Mustafa Odabaşoğluc and Orhan Büyükgüngörb*

aDepartment of Science Education, Sinop University, TR-57100 Sinop, Turkey, bDepartment of Physics, Ondokuz Mayıs University, TR-55139 Samsun, Turkey, and cChemistry Programme, Pamukkale University, TR-20159 Denizli, Turkey
*Correspondence e-mail: bkosar@sinop.edu.tr

(Received 15 December 2009; accepted 28 December 2009; online 9 January 2010)

In the title compound, C15H15NO2, the phenol group make dihedral angles of 2.4 (2) and 24.1 (9)° with the imine linkage (–C=N–) and the phenyl group, respectively, and the mol­ecule adopts the enol–imine tautomeric form, so the mol­ecular structure is stabilized by a strong intra­molecular O—H⋯N hydrogen bond. The crystal structure features a weak C—H⋯π inter­action.

Related literature

For the relationships between thermochromism and photochromism and the planarity of mol­ecules, see: Moustakali-Mavridis et al. (1980[Moustakali-Mavridis, I., Hadjoudis, B. & Mavridis, A. (1980). Acta Cryst. B36, 1126-1130.]). For bond lengths in related structures, see: Tanak & Yavuz (2009[Tanak, H. & Yavuz, M. (2009). J. Molec. Model. DOI 10.1007/s00894-009-0539-5.]); Koşar et al. (2009[Koşar, B., Albayrak, Ç., Odabaşoğlu, M. & Büyükgüngör, O. (2009). Acta Cryst. C65, o517-o520.].

[Scheme 1]

Experimental

Crystal data

  • C15H15NO2

  • Mr = 241.28

  • Monoclinic, C 2/c

  • a = 22.3720 (16) Å

  • b = 7.3191 (4) Å

  • c = 22.1704 (14) Å

  • β = 136.094 (4)°

  • V = 2517.5 (3) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 293 K

  • 0.80 × 0.46 × 0.21 mm
Data collection

  • Stoe IPDS II diffractometer

  • Absorption correction: integration (X-RED; Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED. Stoe & Cie, Darmstadt, Germany.]) Tmin = 0.948, Tmax = 0.984

  • 17732 measured reflections

  • 2914 independent reflections

  • 1935 reflections with I > 2σ(I)

  • Rint = 0.053
Refinement

  • R[F2 > 2σ(F2)] = 0.049

  • wR(F2) = 0.122

  • S = 1.03

  • 2914 reflections

  • 167 parameters

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

  • Δρmax = 0.13 e Å−3

  • Δρmin = −0.12 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1–C6 ring.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H16⋯N1 0.95 (2) 1.75 (2) 2.5992 (19) 148.3 (19)
C15—H15B⋯Cgi 0.96 2.98 3.900 (2) 160
Symmetry code: (i) [-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1].

Data collection: X-AREA (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED. Stoe & Cie, Darmstadt, Germany.]); 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

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809055615/bx2258sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809055615/bx2258Isup2.hkl

checkCIF report


Comment top

Schiff bases are formed by reaction of a primary amine and an aldehyde and have a wide area of usage as ligands in coordination chemistry. Especially o-hydroxy Schiff base derivatives are important classes have attracted the interest of chemists and physicist because of their photochromic and thermochromic features in the solid state. These features are caused by the proton transfer to N atom from O atom with light in photochromic or with temperature in thermochromic Schiff bases. It has been claimed that the molecules showing thermochromism are planar and showing photochromism are non-planar (Moustakali-Mavridis et al., 1980). In general, o-Hydroxy Schiff bases can be found at two possible tautomeric forms called as phenol-imine and keto-amine. The molecular structure of the title compound (I), is the enol-imine tautomer, as indicated by the following bond lengths: N1═C8 (1.284 (2) Å), C8—C9 (1.439 (2) Å) and C10—O1 (1.3445 (18) Å). These bond lengths are in a good agreement with observed for (E)-2-[(4-Chlorophenyl)iminomethyl]-5- methoxyphenol [1.282 (2), 1.436 (2) and 1.3452 (18) Å; Koşar et al., 2009], which is also enol-imine tautomer. The same bond lengths are comparable with observed for (E)-2-[(2-Hydroxy-5-nitrophenyl)-iminomethyl]-4-nitrophenolate [1.288, 1.420 and 1.2749 Å; Tanak & Yavuz, 2009], which is a keto-amine tautomer. The molecule is not planar and make a dihedral angle of 2.4 (2) and 24.1 (9)° with the imine linkage and the phenyl group respectively and shows photochromic features. As a result of enol-imine form of the molecule, there is a strong intramolecular hydrogen bond between the atom O1 and atom N1 (Fig. 1).The crystal structure is primarily determined by one weak C—H···π ( Cg = C1/C6) and van der Waals interactions, Table 1.

Related literature top

For the relationships between thermochromism and photochromism and the planarity of molecules, see: Moustakali-Mavridis et al. (1980). For bond lengths in related structures, see: Tanak & Yavuz (2009); Koşar et al. (2009.

Experimental top

For the preparation of (E)-5-methoxy-2-[(o-tolylimino)methyl]phenol compound the mixture of 4-methoxysalicylaldehyde (0.5 g, 3.3 mmol) in ethanol (20 ml) and 2-methylaniline (0.35 g, 3.3 mmol) in ethanol (20 ml) was stirred for 1 h under reflux. The crystals suitable for X-ray analysis were obtained from ethanol by slow evaporation (yield; %76, m.p.; 372 K).

Refinement top

All H atoms except for H16 were refined using riding model with C—H distances of 0.96 Å for methyl group and 0.93 Å for aromatic groups. The displacement parameters of these H atoms were fixed at 1.2 Ueq of their parent carbon atom for aromatic groups and 1.5 Ueq of their parent atoms for methyl group.

Structure description top

Schiff bases are formed by reaction of a primary amine and an aldehyde and have a wide area of usage as ligands in coordination chemistry. Especially o-hydroxy Schiff base derivatives are important classes have attracted the interest of chemists and physicist because of their photochromic and thermochromic features in the solid state. These features are caused by the proton transfer to N atom from O atom with light in photochromic or with temperature in thermochromic Schiff bases. It has been claimed that the molecules showing thermochromism are planar and showing photochromism are non-planar (Moustakali-Mavridis et al., 1980). In general, o-Hydroxy Schiff bases can be found at two possible tautomeric forms called as phenol-imine and keto-amine. The molecular structure of the title compound (I), is the enol-imine tautomer, as indicated by the following bond lengths: N1═C8 (1.284 (2) Å), C8—C9 (1.439 (2) Å) and C10—O1 (1.3445 (18) Å). These bond lengths are in a good agreement with observed for (E)-2-[(4-Chlorophenyl)iminomethyl]-5- methoxyphenol [1.282 (2), 1.436 (2) and 1.3452 (18) Å; Koşar et al., 2009], which is also enol-imine tautomer. The same bond lengths are comparable with observed for (E)-2-[(2-Hydroxy-5-nitrophenyl)-iminomethyl]-4-nitrophenolate [1.288, 1.420 and 1.2749 Å; Tanak & Yavuz, 2009], which is a keto-amine tautomer. The molecule is not planar and make a dihedral angle of 2.4 (2) and 24.1 (9)° with the imine linkage and the phenyl group respectively and shows photochromic features. As a result of enol-imine form of the molecule, there is a strong intramolecular hydrogen bond between the atom O1 and atom N1 (Fig. 1).The crystal structure is primarily determined by one weak C—H···π ( Cg = C1/C6) and van der Waals interactions, Table 1.

For the relationships between thermochromism and photochromism and the planarity of molecules, see: Moustakali-Mavridis et al. (1980). For bond lengths in related structures, see: Tanak & Yavuz (2009); Koşar et al. (2009.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED (Stoe & Cie, 2002); 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. Thermal ellipsoid view of the title compound. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres with arbitrary radii. Dashed line indicates the intramolecular hydrogen bond.
[Figure 2] Fig. 2. Part of crystal structure of molecule, showing the C—H···π bonds. For clarity, H atoms not included in intermolecular bonding have been omitted. For symmetry codes, see Table 1.
(E)-5-Methoxy-2-(o-tolyliminomethyl)phenol top
Crystal data top
C15H15NO2F(000) = 1024
Mr = 241.28Dx = 1.273 Mg m−3
Monoclinic, C2/cMelting point: 372 K
Hall symbol: -C 2ycMo Kα radiation, λ = 0.71073 Å
a = 22.3720 (16) ÅCell parameters from 2073 reflections
b = 7.3191 (4) Åθ = 1.9–28.0°
c = 22.1704 (14) ŵ = 0.09 mm−1
β = 136.094 (4)°T = 293 K
V = 2517.5 (3) Å3Prism, yellow
Z = 80.80 × 0.46 × 0.21 mm
Data collection top
Stoe IPDS II
diffractometer		2914 independent reflections
Radiation source: fine-focus sealed tube1935 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.053
Detector resolution: 6.67 pixels mm-1θmax = 27.5°, θmin = 2.0°
ω scanh = −28→28
Absorption correction: integration
(X-RED; Stoe & Cie, 2002)		k = −9→9
Tmin = 0.948, Tmax = 0.984l = −28→28
17732 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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0534P)2 + 0.4484P]
where P = (Fo2 + 2Fc2)/3
2914 reflections(Δ/σ)max < 0.001
167 parametersΔρmax = 0.13 e Å−3
0 restraintsΔρmin = −0.12 e Å−3
Crystal data top
C15H15NO2V = 2517.5 (3) Å3
Mr = 241.28Z = 8
Monoclinic, C2/cMo Kα radiation
a = 22.3720 (16) ŵ = 0.09 mm−1
b = 7.3191 (4) ÅT = 293 K
c = 22.1704 (14) Å0.80 × 0.46 × 0.21 mm
β = 136.094 (4)°
Data collection top
Stoe IPDS II
diffractometer		2914 independent reflections
Absorption correction: integration
(X-RED; Stoe & Cie, 2002)		1935 reflections with I > 2σ(I)
Tmin = 0.948, Tmax = 0.984Rint = 0.053
17732 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.122H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.13 e Å−3
2914 reflectionsΔρmin = −0.12 e Å−3
167 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
C10.44408 (9)0.4751 (2)0.61857 (10)0.0585 (4)
C20.48769 (10)0.4298 (2)0.59731 (11)0.0628 (4)
C30.54314 (12)0.5583 (3)0.61274 (13)0.0750 (5)
H30.57340.52930.59980.090*
C40.55431 (13)0.7276 (3)0.64672 (13)0.0829 (6)
H40.59320.81010.65840.100*
C50.50793 (15)0.7743 (3)0.66328 (13)0.0839 (6)
H50.51410.89000.68460.101*
C60.45217 (12)0.6501 (2)0.64842 (11)0.0708 (5)
H60.41980.68330.65840.085*
C70.47509 (15)0.2476 (3)0.55859 (15)0.0866 (6)
H7A0.41560.23320.50440.104*
H7B0.49130.15240.59790.104*
H7C0.51030.24050.54860.104*
C80.37691 (10)0.3374 (2)0.65349 (10)0.0626 (4)
H80.39720.43360.69170.075*
C90.32840 (9)0.1941 (2)0.64692 (9)0.0556 (4)
C100.29831 (9)0.0417 (2)0.59225 (10)0.0543 (4)
C110.25453 (10)−0.0984 (2)0.58927 (10)0.0568 (4)
H110.2359−0.19960.55390.068*
C120.23880 (9)−0.0871 (2)0.63893 (10)0.0555 (4)
C130.26662 (11)0.0640 (2)0.69232 (10)0.0624 (4)
H130.25520.07170.72510.075*
C140.31064 (10)0.2001 (2)0.69596 (10)0.0630 (4)
H140.32950.29990.73200.076*
C150.16589 (13)−0.3735 (3)0.58692 (13)0.0782 (5)
H15A0.2134−0.43520.60260.094*
H15B0.1254−0.33580.52720.094*
H15C0.1381−0.45470.59460.094*
N10.39313 (8)0.33716 (19)0.60847 (8)0.0602 (4)
O10.31237 (8)0.02673 (19)0.54283 (8)0.0683 (3)
O20.19682 (8)−0.21732 (17)0.64089 (8)0.0701 (3)
H160.3415 (14)0.134 (3)0.5514 (14)0.102 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0516 (8)0.0595 (10)0.0495 (8)−0.0007 (7)0.0314 (7)0.0071 (7)
C20.0593 (9)0.0617 (10)0.0615 (9)0.0016 (8)0.0415 (8)0.0104 (8)
C30.0684 (10)0.0764 (12)0.0796 (12)−0.0016 (9)0.0531 (10)0.0124 (10)
C40.0808 (12)0.0762 (14)0.0748 (12)−0.0196 (10)0.0504 (11)0.0049 (10)
C50.1089 (15)0.0595 (11)0.0715 (12)−0.0139 (11)0.0611 (12)−0.0009 (9)
C60.0797 (11)0.0627 (11)0.0640 (10)0.0004 (9)0.0498 (10)0.0056 (8)
C70.1093 (15)0.0689 (12)0.1185 (17)−0.0058 (11)0.0944 (15)−0.0008 (12)
C80.0550 (9)0.0661 (10)0.0533 (9)−0.0033 (7)0.0346 (8)−0.0030 (8)
C90.0513 (8)0.0622 (9)0.0488 (8)−0.0004 (7)0.0345 (7)−0.0003 (7)
C100.0511 (8)0.0643 (10)0.0499 (8)0.0035 (7)0.0371 (7)0.0020 (7)
C110.0560 (8)0.0620 (10)0.0525 (8)−0.0011 (7)0.0390 (7)−0.0040 (7)
C120.0517 (8)0.0647 (10)0.0515 (8)0.0001 (7)0.0377 (7)0.0026 (7)
C130.0675 (9)0.0751 (11)0.0551 (9)−0.0014 (9)0.0476 (8)−0.0041 (8)
C140.0649 (9)0.0677 (10)0.0542 (9)−0.0054 (8)0.0422 (8)−0.0093 (8)
C150.0935 (13)0.0710 (12)0.0880 (13)−0.0158 (10)0.0713 (12)−0.0092 (10)
N10.0544 (7)0.0645 (9)0.0573 (8)−0.0016 (6)0.0387 (7)0.0034 (7)
O10.0801 (8)0.0751 (8)0.0744 (8)−0.0093 (7)0.0640 (7)−0.0089 (6)
O20.0831 (8)0.0741 (8)0.0732 (7)−0.0146 (6)0.0630 (7)−0.0096 (6)
Geometric parameters (Å, º) top
C1—C61.392 (2)C8—H80.9300
C1—C21.395 (2)C9—C141.402 (2)
C1—N11.415 (2)C9—C101.411 (2)
C2—C31.389 (2)C10—O11.3445 (18)
C2—C71.499 (3)C10—C111.387 (2)
C3—C41.376 (3)C11—C121.379 (2)
C3—H30.9300C11—H110.9300
C4—C51.370 (3)C12—O21.3604 (18)
C4—H40.9300C12—C131.397 (2)
C5—C61.378 (3)C13—C141.361 (2)
C5—H50.9300C13—H130.9300
C6—H60.9300C14—H140.9300
C7—H7A0.9600C15—O21.423 (2)
C7—H7B0.9600C15—H15A0.9600
C7—H7C0.9600C15—H15B0.9600
C8—N11.284 (2)C15—H15C0.9600
C8—C91.439 (2)O1—H160.95 (2)
C6—C1—C2119.74 (16)C14—C9—C10117.70 (15)
C6—C1—N1123.08 (16)C14—C9—C8120.87 (15)
C2—C1—N1117.18 (15)C10—C9—C8121.42 (14)
C3—C2—C1118.29 (17)O1—C10—C11118.22 (15)
C3—C2—C7120.63 (17)O1—C10—C9121.17 (15)
C1—C2—C7121.08 (15)C11—C10—C9120.60 (14)
C4—C3—C2121.47 (19)C12—C11—C10119.71 (15)
C4—C3—H3119.3C12—C11—H11120.1
C2—C3—H3119.3C10—C11—H11120.1
C5—C4—C3119.85 (18)O2—C12—C11124.24 (15)
C5—C4—H4120.1O2—C12—C13115.10 (14)
C3—C4—H4120.1C11—C12—C13120.65 (15)
C4—C5—C6120.1 (2)C14—C13—C12119.43 (15)
C4—C5—H5120.0C14—C13—H13120.3
C6—C5—H5120.0C12—C13—H13120.3
C5—C6—C1120.39 (19)C13—C14—C9121.88 (16)
C5—C6—H6119.8C13—C14—H14119.1
C1—C6—H6119.8C9—C14—H14119.1
C2—C7—H7A109.5O2—C15—H15A109.5
C2—C7—H7B109.5O2—C15—H15B109.5
H7A—C7—H7B109.5H15A—C15—H15B109.5
C2—C7—H7C109.5O2—C15—H15C109.5
H7A—C7—H7C109.5H15A—C15—H15C109.5
H7B—C7—H7C109.5H15B—C15—H15C109.5
N1—C8—C9122.35 (16)C8—N1—C1121.51 (15)
N1—C8—H8118.8C10—O1—H16107.6 (13)
C9—C8—H8118.8C12—O2—C15117.67 (13)
C6—C1—C2—C34.6 (2)C8—C9—C10—C11177.51 (14)
N1—C1—C2—C3−175.30 (14)O1—C10—C11—C12−179.80 (14)
C6—C1—C2—C7−175.26 (16)C9—C10—C11—C121.3 (2)
N1—C1—C2—C74.9 (2)C10—C11—C12—O2−179.71 (14)
C1—C2—C3—C4−1.1 (3)C10—C11—C12—C13−0.1 (2)
C7—C2—C3—C4178.75 (18)O2—C12—C13—C14178.83 (15)
C2—C3—C4—C5−2.2 (3)C11—C12—C13—C14−0.8 (2)
C3—C4—C5—C62.0 (3)C12—C13—C14—C90.6 (2)
C4—C5—C6—C11.6 (3)C10—C9—C14—C130.6 (2)
C2—C1—C6—C5−4.9 (2)C8—C9—C14—C13−178.44 (15)
N1—C1—C6—C5174.98 (15)C9—C8—N1—C1−177.22 (14)
N1—C8—C9—C14−178.93 (15)C6—C1—N1—C8−25.8 (2)
N1—C8—C9—C102.1 (2)C2—C1—N1—C8154.04 (15)
C14—C9—C10—O1179.60 (14)C11—C12—O2—C15−1.2 (2)
C8—C9—C10—O1−1.4 (2)C13—C12—O2—C15179.16 (15)
C14—C9—C10—C11−1.5 (2)
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C1–C6 ring.
D—H···AD—HH···AD···AD—H···A
O1—H16···N10.95 (2)1.75 (2)2.5992 (19)148.3 (19)
C15—H15B···Cgi0.962.983.900 (2)160
Symmetry code: (i) −x+1/2, −y+1/2, −z+1.

Experimental details

Crystal data
Chemical formulaC15H15NO2
Mr241.28
Crystal system, space groupMonoclinic, C2/c
Temperature (K)293
a, b, c (Å)22.3720 (16), 7.3191 (4), 22.1704 (14)
β (°) 136.094 (4)
V (Å3)2517.5 (3)
Z8
Radiation typeMo Kα
µ (mm−1)0.09
Crystal size (mm)0.80 × 0.46 × 0.21
Data collection
DiffractometerStoe IPDS II
Absorption correctionIntegration
(X-RED; Stoe & Cie, 2002)
Tmin, Tmax0.948, 0.984
No. of measured, independent and
observed [I > 2σ(I)] reflections		17732, 2914, 1935
Rint0.053
(sin θ/λ)max (Å−1)0.651
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.122, 1.03
No. of reflections2914
No. of parameters167
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.13, −0.12

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C1–C6 ring.
D—H···AD—HH···AD···AD—H···A
O1—H16···N10.95 (2)1.75 (2)2.5992 (19)148.3 (19)
C15—H15B···Cgi0.962.983.900 (2)160.26
Symmetry code: (i) −x+1/2, −y+1/2, −z+1.
 

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayis University, Turkey, for the use of the diffractometer (purchased under grant F.279 of University Research Fund).

References

First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
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 First citationKoşar, B., Albayrak, Ç., Odabaşoğlu, M. & Büyükgüngör, O. (2009). Acta Cryst. C65, o517–o520.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationMoustakali-Mavridis, I., Hadjoudis, B. & Mavridis, A. (1980). Acta Cryst. B36, 1126–1130.  CSD CrossRef CAS IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationStoe & Cie (2002). X-AREA and X-RED. Stoe & Cie, Darmstadt, Germany.  Google Scholar
 First citationTanak, H. & Yavuz, M. (2009). J. Molec. Model. DOI 10.1007/s00894-009-0539-5.  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.

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ISSN: 2056-9890
Volume 66| Part 2| February 2010| Page o311
https://doi.org/10.1107/S1600536809055615
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