(E,E)-1-(2-Hydroxy­imino-1-phenyl­ethyl­idene)semicarbazide monohydrate

Öztürk, A.; Babahan, İ.; Sarıkavaklı, N.; Hökelek, T.

doi:10.1107/S1600536809013865

organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Pages o1059-o1060

doi:10.1107/S1600536809013865

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(E,E)-1-(2-Hydroxyimino-1-phenylethylidene)semicarbazide monohydrate

Aslı Öztürk,^a İlknur Babahan,^b Nursabah Sarıkavaklı ^b and Tuncer Hökelek ^a ^*

^aHacettepe University, Department of Physics, 06800 Beytepe, Ankara, Turkey, and ^bAdnan Menderes University, Department of Chemistry, 09010 Aydın, Turkey
^*Correspondence e-mail: merzifon@hacettepe.edu.tr

(Received 23 March 2009; accepted 13 April 2009; online 18 April 2009)

In the title compound, C₉H₁₀N₄O₂·H₂O, the oxime unit has an E configuration, and an intramolecular N—H⋯N hydrogen bond results in the formation of a planar five-membered ring, which is oriented with respect to the aromatic ring at a dihedral angle of 74.82 (17)°. In the crystal structure, intermolecular O—H⋯O and N—H⋯O hydrogen bonds link the molecules and R₂²(8) ring motifs are apparent.

Related literature

For general background, see: Balsamo et al. (1990 ); Marsman et al. (1999 ); Karle et al. (1996 ); Etter et al. (1990 ). For related structures, see: Sarıkavaklı et al. (2007 , 2008 ); Özel Güven et al. (2007 ); Hökelek, Batı et al. (2001 ); Hökelek, Zülfikaroğlu et al. (2001 ); Büyükgüngör et al. (2003 ); Hökelek et al. (2004 ); Hökelek et al. (2004a ,b ). For reference structural data, see: Allen et al. (1987 ). For ring motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₉H₁₀N₄O₂·H₂O
M_r = 224.23
Triclinic, $[P \overline 1]$
a = 5.5593 (2) Å
b = 8.2701 (3) Å
c = 12.6193 (5) Å
α = 71.900 (3)°
β = 89.998 (5)°
γ = 78.538 (5)°
V = 539.29 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 294 K
0.40 × 0.25 × 0.20 mm

Data collection

Enraf–Nonius TurboCAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.968, T_max = 0.978
1953 measured reflections
1752 independent reflections
867 reflections with I > 2σ(I)
R_int = 0.048
3 standard reflections frequency: 120 min intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.185
S = 1.05
1752 reflections
171 parameters
5 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯N1	0.88 (3)	2.32 (6)	2.647 (8)	102 (5)
O3—H31⋯O1	0.88 (7)	1.92 (8)	2.776 (9)	164 (8)
O3—H32⋯O3ⁱ	0.90 (3)	2.17 (7)	2.909 (11)	140 (7)
N2—H22⋯O3ⁱⁱ	0.82 (3)	2.10 (4)	2.901 (10)	162 (5)
N3—H3B⋯O1ⁱⁱⁱ	0.96 (7)	1.96 (6)	2.909 (8)	169 (6)
Symmetry codes: (i) -x, -y, -z+2; (ii) -x+1, -y, -z+2; (iii) -x+1, -y-1, -z+2.

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); 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 Mercury (Macrae et al., 2006 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809013865/hb2932sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809013865/hb2932Isup2.hkl

checkCIF report

Comment top

Oxime and dioxime derivatives have a broad pharmacological activity spectrum, encompassing antibacterial, antidepressant and antifungal activities (e.g. Balsamo et al., 1990). The oxime (–C=N—OH) moiety is potentially ambidentate, with possibilities of coordination to metal ions through nitrogen and/or oxygen atoms. Oxime groups possess stronger hydrogen-bonding capabilities than alcohols, phenols, and carboxylic acids (Marsman et al., 1999), in which intermolecular hydrogen bonding combines moderate strength and directionality (Karle et al., 1996) in linking molecules to form supramolecular structures; this has received considerable attention with respect to directional noncovalent intermolecular interactions (Etter et al., 1990).

The structures of some oxime and dioxime derivatives have been determined in our laboratory, including those of 2,3-dimethylquinoxaline-dimethyl-glyoxime (1/1), [(II) Hökelek, Batı et al., 2001], 1-(2,6-dimethylphenylamino) propane-1,2-dione dioxime, [(III) (Hökelek, Zülfikaroğlu et al., 2001), N-hydroxy-2-oxo-2,N'-diphenylacetamidine, [(IV) (Büyükgüngör et al., 2003], N-(3,4-dichlorophenyl)-N'-hydroxy-2-oxo-2-phenylacetamidine, [(V) Hökelek et al., 2004], N-hydroxy-N'-(1-naphthyl)-2-phenylacetamidin-2-one [(VI) Hökelek et al., 2004a], N-(3-chloro-4-methylphenyl)-N'-hydroxy-2 -oxo-2-phenylacetamidine [(VII) Hökelek et al., 2004b], 2-(1H-benzimidazol -1-yl)-1-phenylethanone oxime [(VIII) Özel Güven et al., 2007], (1Z,2E)-1-(3,5-dimethyl-1H-pyrazole-1-yl)ethane-1,2-dione dioxime [(IX) Sarıkavaklı et al., 2007] and 2-hydroxyimino-1-phenylethanone thiosemicar bazone monohydrate [(X) Sarıkavaklı et al., 2008].

As part of our ongoing studies in this area, the structure determination of the title compound, (I), an oxime derivative with one semicarbazide, one phenylacetaldehyde oxime moieties and one uncoordinated water molecule, was carried out in order to investigate the strength of the hydrogen bonding capability of the oxime and semicarbazide groups and to compare the geometry of the oxime moiety with the previously reported ones.

In the molecule of the title compound, (I), (Fig. 1) the bond lengths (Allen et al., 1987) and angles are generally within normal ranges. Ring A (C1—C6) is, of course, planar. The intramolecular N—H···N hydrogen bond (Table 1) results in the formation of a planar five-membered ring B (N1—N3/C8/H3A). The dihedral angle between the planar rings is A/B = 74.82 (17)°.

In the crystal structure, intramolecular O—H···O and N—H···N and intermolecular O—H···O and N—H···O hydrogen bonds (Table 1) link the molecules through R₂²(8) ring motifs (Bernstein et al., 1995) (Fig. 2).

Related literature top

For general background, see: Balsamo et al. (1990); Marsman et al. (1999); Karle et al. (1996); Etter et al. (1990). For related structures, see: Sarıkavaklı et al. (2007, 2008); Özel Güven et al. (2007); Hökelek, Batı et al. (2001); Hökelek, Zülfikaroğlu et al. (2001); Büyükgüngör et al. (2003); Hökelek et al. (2004); Hökelek et al. (2004a,b). For reference structural data, see: Allen et al. (1987). For ring motifs, see: Bernstein et al. (1995).

Experimental top

Semicarbazide hydrochloride (1.12 g, 10 mmol) and sodium acetate (0.82 g, 10 mmol) were dissolved in double distilled water in the molar ratio 1:1. Then, the solution was mixed with a solution of 2-isonitrosoacetophenone (1.49 g, 10 mmol) in ethanol (10 ml) yielding a turbid mixture. The excess ethanol was added to get a clear solution and was stirred in a magnetic stirrer at room temparature for 4 h. The precipitate formed was filtered, washed with water and dried at room temperature in vacuum desiccator. It was recrystallized from ethanol/water (2:1) solution to yield colourless prisms of (I) (yield; 1.80 g, 85%, m.p. 409 K).

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995); 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 Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of (I) with displacement ellipsoids for the non-hydrogen atoms drawn at the 50% probability level. Hydrogen bonds are shown as dashed lines.
	Fig. 2. A partial packing diagram of (I). Hydrogen bonds are shown as dotted lines.

(E,E)-1-(2-Hydroxyimino-1-phenylethylidene)semicarbazide monohydrate top

Crystal data top

C₉H₁₀N₄O₂·H₂O	Z = 2
M_r = 224.23	F(000) = 236
Triclinic, P1	D_x = 1.381 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.5593 (2) Å	Cell parameters from 25 reflections
b = 8.2701 (3) Å	θ = 8.6–17.3°
c = 12.6193 (5) Å	µ = 0.11 mm⁻¹
α = 71.900 (3)°	T = 294 K
β = 89.998 (5)°	Prism, colorless
γ = 78.538 (5)°	0.40 × 0.25 × 0.20 mm
V = 539.29 (4) Å³

Data collection top

Enraf–Nonius TurboCAD-4 diffractometer	867 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.048
Graphite monochromator	θ_max = 24.3°, θ_min = 3.4°
Non–profiled ω scans	h = −6→0
Absorption correction: ψ scan (North et al., 1968)	k = −9→9
T_min = 0.968, T_max = 0.978	l = −14→14
1953 measured reflections	3 standard reflections every 120 min
1752 independent reflections	intensity decay: 1%

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.185	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0859P)²] where P = (F_o² + 2F_c²)/3
1752 reflections	(Δ/σ)_max < 0.001
171 parameters	Δρ_max = 0.19 e Å⁻³
5 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₉H₁₀N₄O₂·H₂O	γ = 78.538 (5)°
M_r = 224.23	V = 539.29 (4) Å³
Triclinic, P1	Z = 2
a = 5.5593 (2) Å	Mo Kα radiation
b = 8.2701 (3) Å	µ = 0.11 mm⁻¹
c = 12.6193 (5) Å	T = 294 K
α = 71.900 (3)°	0.40 × 0.25 × 0.20 mm
β = 89.998 (5)°

Data collection top

Enraf–Nonius TurboCAD-4 diffractometer	867 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.048
T_min = 0.968, T_max = 0.978	3 standard reflections every 120 min
1953 measured reflections	intensity decay: 1%
1752 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	5 restraints
wR(F²) = 0.185	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.19 e Å⁻³
1752 reflections	Δρ_min = −0.34 e Å⁻³
171 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

	x	y	z	U_iso*/U_eq
O1	0.5650 (8)	−0.2847 (5)	0.9749 (4)	0.0635 (13)
O2	1.6136 (8)	−0.2215 (5)	0.5421 (4)	0.0583 (13)
H21	1.658 (12)	−0.131 (10)	0.490 (6)	0.09 (3)*
O3	0.2334 (12)	−0.0741 (10)	1.0657 (7)	0.132 (3)
H31	0.344 (10)	−0.122 (11)	1.028 (6)	0.125*
H32	0.088 (7)	−0.084 (10)	1.041 (7)	0.125*
N1	1.0377 (8)	−0.2812 (6)	0.7948 (4)	0.0456 (13)
N2	0.8573 (9)	−0.2253 (6)	0.8554 (4)	0.0498 (14)
H22	0.823 (9)	−0.128 (4)	0.863 (4)	0.040 (17)*
N3	0.7601 (11)	−0.4938 (7)	0.9070 (5)	0.0594 (16)
H3A	0.884 (8)	−0.531 (8)	0.872 (5)	0.08 (2)*
H3B	0.665 (11)	−0.578 (9)	0.942 (5)	0.08 (2)*
N4	1.4358 (8)	−0.1346 (5)	0.5950 (4)	0.0435 (13)
C1	1.0910 (10)	0.0218 (7)	0.7132 (5)	0.0389 (14)
C2	1.2415 (11)	0.0996 (7)	0.7590 (5)	0.0538 (17)
H2	1.3800	0.0317	0.8044	0.065*
C3	1.1895 (12)	0.2758 (8)	0.7384 (6)	0.0646 (19)
H3	1.2905	0.3257	0.7719	0.077*
C4	0.9938 (13)	0.3786 (8)	0.6700 (6)	0.0602 (18)
H4	0.9626	0.4987	0.6543	0.072*
C5	0.8426 (12)	0.3024 (8)	0.6244 (5)	0.065 (2)
H5	0.7064	0.3716	0.5778	0.078*
C6	0.8891 (12)	0.1243 (8)	0.6466 (5)	0.0591 (18)
H6	0.7829	0.0742	0.6162	0.071*
C7	1.1479 (10)	−0.1688 (6)	0.7314 (4)	0.0387 (14)
C8	0.7189 (11)	−0.3364 (7)	0.9167 (5)	0.0455 (15)
C9	1.3383 (11)	−0.2382 (8)	0.6696 (5)	0.0444 (15)
H9	1.374 (10)	−0.359 (9)	0.687 (5)	0.064 (19)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.066 (3)	0.051 (3)	0.078 (3)	−0.018 (2)	0.036 (3)	−0.024 (2)
O2	0.062 (3)	0.044 (3)	0.064 (3)	−0.005 (2)	0.026 (2)	−0.014 (2)
O3	0.106 (5)	0.148 (6)	0.173 (7)	0.002 (5)	0.008 (5)	−0.111 (5)
N1	0.049 (3)	0.041 (3)	0.048 (3)	−0.012 (2)	0.017 (3)	−0.013 (2)
N2	0.058 (3)	0.036 (3)	0.057 (3)	−0.015 (3)	0.019 (3)	−0.014 (3)
N3	0.065 (4)	0.043 (3)	0.076 (4)	−0.022 (3)	0.030 (3)	−0.019 (3)
N4	0.046 (3)	0.037 (3)	0.046 (3)	−0.006 (2)	0.009 (2)	−0.012 (2)
C1	0.038 (3)	0.035 (3)	0.041 (3)	−0.007 (3)	0.011 (3)	−0.010 (3)
C2	0.050 (4)	0.042 (4)	0.066 (4)	−0.005 (3)	−0.008 (3)	−0.014 (3)
C3	0.062 (4)	0.046 (4)	0.089 (5)	−0.016 (4)	−0.003 (4)	−0.024 (4)
C4	0.074 (5)	0.035 (3)	0.071 (5)	−0.013 (4)	0.013 (4)	−0.016 (3)
C5	0.068 (5)	0.045 (4)	0.067 (5)	0.010 (4)	−0.011 (4)	−0.007 (4)
C6	0.060 (4)	0.045 (4)	0.065 (4)	−0.008 (3)	−0.014 (4)	−0.010 (3)
C7	0.043 (3)	0.032 (3)	0.037 (3)	−0.009 (3)	0.002 (3)	−0.005 (3)
C8	0.049 (4)	0.035 (3)	0.046 (4)	−0.009 (3)	0.012 (3)	−0.005 (3)
C9	0.051 (4)	0.031 (3)	0.051 (4)	−0.011 (3)	0.007 (3)	−0.012 (3)

Geometric parameters (Å, º) top

O1—C8	1.226 (6)	C2—H2	0.9300
O2—N4	1.399 (5)	C3—H3	0.9300
O2—H21	0.91 (8)	C4—C3	1.352 (9)
O3—H31	0.88 (7)	C4—C5	1.368 (9)
O3—H32	0.90 (3)	C4—H4	0.9300
N1—C7	1.281 (6)	C5—C6	1.381 (8)
N2—N1	1.357 (6)	C5—H5	0.9300
N2—C8	1.369 (7)	C6—H6	0.9300
N2—H22	0.82 (3)	C7—C1	1.489 (7)
N3—H3A	0.88 (3)	C8—N3	1.320 (7)
N3—H3B	0.96 (7)	C9—N4	1.264 (7)
C1—C2	1.376 (8)	C9—C7	1.447 (7)
C1—C6	1.365 (8)	C9—H9	0.94 (6)
C2—C3	1.368 (8)

N4—O2—H21	101 (4)	C3—C4—C5	118.6 (6)
H31—O3—H32	105 (4)	C3—C4—H4	120.7
C7—N1—N2	118.1 (5)	C5—C4—H4	120.7
N1—N2—C8	120.5 (5)	C4—C5—C6	121.0 (6)
N1—N2—H22	126 (4)	C4—C5—H5	119.5
C8—N2—H22	113 (4)	C6—C5—H5	119.5
C8—N3—H3A	122 (4)	C1—C6—C5	120.0 (6)
C8—N3—H3B	123 (4)	C1—C6—H6	120.0
H3A—N3—H3B	115 (6)	C5—C6—H6	120.0
C9—N4—O2	112.3 (4)	N1—C7—C1	126.4 (5)
C2—C1—C7	121.7 (5)	N1—C7—C9	114.9 (5)
C6—C1—C2	118.6 (5)	C9—C7—C1	118.7 (5)
C6—C1—C7	119.7 (5)	O1—C8—N2	119.1 (5)
C1—C2—H2	119.7	O1—C8—N3	124.4 (6)
C3—C2—C1	120.7 (6)	N3—C8—N2	116.5 (5)
C3—C2—H2	119.7	N4—C9—C7	119.3 (5)
C2—C3—H3	119.5	N4—C9—H9	125 (4)
C4—C3—C2	121.1 (6)	C7—C9—H9	116 (3)
C4—C3—H3	119.5

N2—N1—C7—C1	−2.8 (8)	C5—C4—C3—C2	2.2 (10)
N2—N1—C7—C9	179.9 (5)	C3—C4—C5—C6	−0.6 (10)
C8—N2—N1—C7	174.2 (5)	C4—C5—C6—C1	−1.2 (10)
N1—N2—C8—O1	176.6 (5)	N1—C7—C1—C2	106.3 (7)
N1—N2—C8—N3	−4.4 (8)	N1—C7—C1—C6	−75.8 (8)
C6—C1—C2—C3	0.1 (9)	C9—C7—C1—C2	−76.5 (7)
C7—C1—C2—C3	178.0 (6)	C9—C7—C1—C6	101.4 (6)
C2—C1—C6—C5	1.4 (9)	N4—C9—C7—N1	171.4 (5)
C7—C1—C6—C5	−176.5 (6)	N4—C9—C7—C1	−6.1 (8)
C1—C2—C3—C4	−2.0 (10)	C7—C9—N4—O2	−179.2 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N1	0.88 (3)	2.32 (6)	2.647 (8)	102 (5)
O3—H31···O1	0.88 (7)	1.92 (8)	2.776 (9)	164 (8)
O3—H32···O3ⁱ	0.90 (3)	2.17 (7)	2.909 (11)	140 (7)
N2—H22···O3ⁱⁱ	0.82 (3)	2.10 (4)	2.901 (10)	162 (5)
N3—H3B···O1ⁱⁱⁱ	0.96 (7)	1.96 (6)	2.909 (8)	169 (6)

Symmetry codes: (i) −x, −y, −z+2; (ii) −x+1, −y, −z+2; (iii) −x+1, −y−1, −z+2.

Experimental details

Crystal data
Chemical formula	C₉H₁₀N₄O₂·H₂O
M_r	224.23
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	5.5593 (2), 8.2701 (3), 12.6193 (5)
α, β, γ (°)	71.900 (3), 89.998 (5), 78.538 (5)
V (Å³)	539.29 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.40 × 0.25 × 0.20

Data collection
Diffractometer	Enraf–Nonius TurboCAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.968, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	1953, 1752, 867
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.579

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.185, 1.05
No. of reflections	1752
No. of parameters	171
No. of restraints	5
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.34

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N1	0.88 (3)	2.32 (6)	2.647 (8)	102 (5)
O3—H31···O1	0.88 (7)	1.92 (8)	2.776 (9)	164 (8)
O3—H32···O3ⁱ	0.90 (3)	2.17 (7)	2.909 (11)	140 (7)
N2—H22···O3ⁱⁱ	0.82 (3)	2.10 (4)	2.901 (10)	162 (5)
N3—H3B···O1ⁱⁱⁱ	0.96 (7)	1.96 (6)	2.909 (8)	169 (6)

Symmetry codes: (i) −x, −y, −z+2; (ii) −x+1, −y, −z+2; (iii) −x+1, −y−1, −z+2.

Acknowledgements

The authors acknowledge the purchase of the CAD-4 diffractometer under grant DPT/TBAG1 of the Scientific and Technical Research Council of Turkey.

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