Ethyl 4-(3-ethyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-4-yl)benzoate

Ünver, Y.; Köysal, Y.; Tanak, H.; Ünlüer, D.; Işık, Ş.

doi:10.1107/S160053681001603X

organic compounds

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Volume 66| Part 6| June 2010| Page o1294

https://doi.org/10.1107/S160053681001603X

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Ethyl 4-(3-ethyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-4-yl)benzoate

Yasemin Ünver,^a Yavuz Köysal,^b ^* Hasan Tanak,^c Dilek Ünlüer ^a and Şamil Işık ^c

^aDepartment of Chemistry, Karadeniz Technical University, TR-61080 Trabzon, Turkey, ^bSamsun Vocational School, Ondokuz Mayıs University, TR-55139 Samsun, Turkey, and ^cDepartment of Physics, Ondokuz Mayıs University, TR-55139, Samsun, Turkey
^*Correspondence e-mail: yavuzk@omu.edu.tr

(Received 29 April 2010; accepted 30 April 2010; online 8 May 2010)

In the title compound, C₁₃H₁₅N₃O₃, the dihedral angle between the two aromatic ring is 51.06 (1)°. In the crystal, molecules are connected by pairs of N—H⋯O hydrogen bonds into centrosymmetric dimers.

Related literature

For the pharmacological activity of 1,2,4-triazole compounds, see: Chiu & Huskey (1998 ); Eliott et al. (1986 , 1987 ); Griffin & Mannion (1986 , 1987, 1987 ); Heubach et al. (1975 , 1979 ); Husain & Amir (1986 , 1987 ,); Tanaka (1974 , 1975 ); Tsukuda et al. (1998 ); Witkoaski et al. (1972 ). For the biological activity of the triazole family, see: Unver et al. (2008 , 2009 ). For a related structure, see: Tanak et al. (2010 ).

Experimental

Crystal data

C₁₃H₁₅N₃O₃
M_r = 261.28
Monoclinic, P 2₁ /n
a = 13.6111 (11) Å
b = 4.0970 (2) Å
c = 24.172 (2) Å
β = 100.063 (7)°
V = 1327.20 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.80 × 0.41 × 0.13 mm

Data collection

Stoe IPDS 2 diffractometer
8189 measured reflections
2581 independent reflections
1606 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.095
S = 0.93
2581 reflections
216 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.883 (19)	1.94 (2)	2.808 (2)	169.5 (18)
Symmetry code: (i) -x+1, -y+2, -z.

Data collection: X-AREA (Stoe & Cie, 2002 ); cell refinement: X-AREA; data reduction: X-RED32 (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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053681001603X/bt5258sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681001603X/bt5258Isup2.hkl

checkCIF report

Comment top

1,2,4-triazole compounds posses important pharmacology activities such as antifungal and antiviral activities. Examples of such compounds bearing the 1,2,4- triazole residues are fluconazole (Tsukuda et al., 1998), the powerful azole antifungal agent as well as the potent antiviral N- nucleoside ribavirin (Witkoaski et al., 1972). Furthermore, various 1,2,4-triazole derivatives have been reported as fungicidal (Heubach et al., 1975, 1979), insecticidal (Tanaka, 1974, 1975), antimicrobial, (Griffin & Mannion, 1986, 1987) as well as anticonvulsants (Husain & Amir, 1986, 1987), antidepressants (Chiu & Huskey, 1998), and plant growth regulator anticoagulants (Eliott et al., 1986, 1987). Our laboratories reported the some biological activity of the triazole family (Unver et al., 2008; Unver et al., 2009). It is known that 1,2,4-triazol moieties interact strongly with heme iron, and aromatic substituents on the triazoles are very effective for interacting with the active site of aromatase. Furthermore, It was reported that compounds having triazole moieties such as Vorozole, Anastrozole and Letrozole appear to be very effective aromatase inhibitors very useful for preventing breast cancer.

In the title compound, the plane of the -C(=O)—O- group is inclined at the angle of 4.23 (1)° with respect to the benzoate ring. The dihedral angle between the two aromatic ring is 51.06 (1)°. The 1,2,4-triazole ring is strictly planar and the maximum deviation of -0.0016 (2)Å for atom C1. The double bond distance in the triazol group is good agreement with our previous report,5-benzyl-4- (3,4-dimethoxyphenethyl)-2H-1,2,4-triazol-3(4H)-one (Tanak et al., 2010).

The molecules are connected by intermolecular N—H···O hydrogen bonds to centrosymmetric dimers. generating eight-membered ring, producing a R₂²(8) motif (Bernstein et al., 1995).

Related literature top

For the pharmacological activity of 1,2,4-triazole compounds, see: Chiu & Huskey (1998); Eliott et al. (1986, 1987); Griffin & Mannion (1986, 1987, 1987); Heubach et al. (1975, 1979); Husain & Amir (1986, 1987,); Tanaka (1974, 1975); Tsukuda et al. (1998); Witkoaski et al. (1972). For the biological activity of the triazole family, see: Unver et al. (2008, 2009). For a related structure, see: Tanak et al. (2010).

Experimental top

Ethyl 2-(1-ethoxypropylidene)hydrazinecarboxylate (10 mmol) and ethyl 4-amino benzoate (10 mmol) was mixed without solvent and heated at 433-443°K for 2 h. The formed solid products were separated by filtration, purified by crystallization twice from ethanol, washed with Et₂O ether and dried in a vacuum. m p: 446°K.

Structure description top

The molecules are connected by intermolecular N—H···O hydrogen bonds to centrosymmetric dimers. generating eight-membered ring, producing a R₂²(8) motif (Bernstein et al., 1995).

For the pharmacological activity of 1,2,4-triazole compounds, see: Chiu & Huskey (1998); Eliott et al. (1986, 1987); Griffin & Mannion (1986, 1987, 1987); Heubach et al. (1975, 1979); Husain & Amir (1986, 1987,); Tanaka (1974, 1975); Tsukuda et al. (1998); Witkoaski et al. (1972). For the biological activity of the triazole family, see: Unver et al. (2008, 2009). For a related structure, see: Tanak et al. (2010).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (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

	Fig. 1. A view of the title compound with the atom-numbering scheme and 50% probability displacement ellipsoids.
	Fig. 2. A partial packing diagram of the title compound.

Ethyl 4-(3-ethyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-4-yl)benzoate top

Crystal data top

C₁₃H₁₅N₃O₃	F(000) = 552
M_r = 261.28	D_x = 1.308 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 13.6111 (11) Å	Cell parameters from 10833 reflections
b = 4.0970 (2) Å	θ = 1.5–27.2°
c = 24.172 (2) Å	µ = 0.10 mm⁻¹
β = 100.063 (7)°	T = 293 K
V = 1327.20 (17) Å³	Prism, colourless
Z = 4	0.80 × 0.41 × 0.13 mm

Data collection top

Stoe IPDS 2 diffractometer	1606 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.042
Graphite monochromator	θ_max = 26.0°, θ_min = 1.6°
Detector resolution: 6.67 pixels mm^-1	h = −16→15
rotation method scans	k = −4→5
8189 measured reflections	l = −29→29
2581 independent reflections

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 0.93	w = 1/[σ²(F_o²) + (0.0488P)²] where P = (F_o² + 2F_c²)/3
2581 reflections	(Δ/σ)_max < 0.001
216 parameters	Δρ_max = 0.13 e Å⁻³
0 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₁₃H₁₅N₃O₃	V = 1327.20 (17) Å³
M_r = 261.28	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.6111 (11) Å	µ = 0.10 mm⁻¹
b = 4.0970 (2) Å	T = 293 K
c = 24.172 (2) Å	0.80 × 0.41 × 0.13 mm
β = 100.063 (7)°

Data collection top

Stoe IPDS 2 diffractometer	1606 reflections with I > 2σ(I)
8189 measured reflections	R_int = 0.042
2581 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 0.93	Δρ_max = 0.13 e Å⁻³
2581 reflections	Δρ_min = −0.14 e Å⁻³
216 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
C1	0.44143 (13)	0.7739 (5)	0.05726 (6)	0.0485 (5)
C2	0.51671 (12)	0.5332 (4)	0.13682 (6)	0.0440 (4)
C3	0.53173 (14)	0.3581 (6)	0.19150 (8)	0.0525 (5)
C4	0.63819 (16)	0.2621 (7)	0.21203 (9)	0.0631 (6)
C5	0.32736 (11)	0.5585 (5)	0.11912 (6)	0.0432 (4)
C6	0.30553 (12)	0.6504 (5)	0.17095 (6)	0.0466 (5)
H6	0.3534	0.7542	0.1973	0.056*
C7	0.21229 (12)	0.5858 (5)	0.18282 (6)	0.0473 (4)
H7	0.1975	0.6437	0.2177	0.057*
C8	0.14040 (12)	0.4365 (5)	0.14379 (6)	0.0450 (4)
C9	0.16301 (13)	0.3535 (5)	0.09164 (7)	0.0533 (5)
H9	0.1146	0.2559	0.0648	0.064*
C10	0.25609 (12)	0.4141 (5)	0.07938 (6)	0.0515 (5)
H10	0.2708	0.3579	0.0445	0.062*
C11	0.04218 (13)	0.3608 (5)	0.15961 (7)	0.0512 (5)
C12	−0.11800 (16)	0.1271 (8)	0.13044 (10)	0.0724 (7)
C13	−0.1753 (2)	−0.0096 (12)	0.07756 (15)	0.1015 (11)
N1	0.54074 (11)	0.7686 (5)	0.06243 (6)	0.0562 (5)
N2	0.58809 (10)	0.6223 (4)	0.11107 (5)	0.0519 (4)
N3	0.42458 (9)	0.6181 (4)	0.10615 (5)	0.0447 (4)
O1	0.37870 (9)	0.8859 (4)	0.01948 (5)	0.0624 (4)
O2	0.02253 (9)	0.4134 (4)	0.20563 (5)	0.0726 (5)
O3	−0.02131 (9)	0.2283 (4)	0.11801 (5)	0.0660 (4)
H1	0.5731 (14)	0.864 (5)	0.0382 (8)	0.062 (6)*
H3A	0.4910 (15)	0.170 (5)	0.1871 (8)	0.069 (6)*
H3B	0.5059 (14)	0.489 (5)	0.2178 (8)	0.065 (6)*
H4A	0.6436 (14)	0.140 (5)	0.2481 (9)	0.074 (6)*
H4B	0.6795 (18)	0.443 (6)	0.2188 (9)	0.090 (8)*
H4C	0.6648 (16)	0.115 (6)	0.1853 (10)	0.086 (7)*
H12A	−0.1044 (16)	−0.029 (6)	0.1621 (9)	0.085 (7)*
H12B	−0.1459 (17)	0.324 (6)	0.1422 (9)	0.083 (8)*
H13A	−0.234 (2)	−0.096 (8)	0.0840 (12)	0.126 (10)*
H13B	−0.138 (3)	−0.175 (9)	0.0604 (14)	0.153 (16)*
H13C	−0.189 (2)	0.174 (8)	0.0528 (12)	0.120 (12)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0429 (10)	0.0675 (13)	0.0373 (8)	−0.0030 (9)	0.0133 (7)	0.0024 (9)
C2	0.0395 (9)	0.0531 (12)	0.0399 (8)	−0.0052 (8)	0.0087 (7)	−0.0039 (8)
C3	0.0470 (11)	0.0639 (15)	0.0468 (10)	0.0000 (11)	0.0083 (8)	0.0064 (10)
C4	0.0521 (12)	0.0768 (17)	0.0572 (12)	0.0002 (13)	0.0006 (10)	0.0093 (12)
C5	0.0374 (9)	0.0534 (12)	0.0404 (8)	−0.0005 (8)	0.0111 (7)	0.0043 (8)
C6	0.0433 (9)	0.0591 (13)	0.0377 (8)	−0.0077 (9)	0.0083 (7)	−0.0033 (8)
C7	0.0462 (9)	0.0612 (12)	0.0364 (8)	−0.0028 (9)	0.0127 (7)	−0.0011 (8)
C8	0.0377 (9)	0.0572 (12)	0.0409 (8)	0.0010 (8)	0.0095 (7)	0.0033 (8)
C9	0.0431 (10)	0.0739 (14)	0.0428 (9)	−0.0079 (9)	0.0074 (7)	−0.0078 (9)
C10	0.0449 (10)	0.0743 (13)	0.0370 (8)	−0.0026 (10)	0.0118 (7)	−0.0052 (9)
C11	0.0417 (10)	0.0646 (14)	0.0481 (9)	−0.0004 (9)	0.0095 (8)	0.0047 (9)
C12	0.0435 (12)	0.096 (2)	0.0784 (15)	−0.0156 (13)	0.0131 (11)	0.0078 (15)
C13	0.0636 (17)	0.135 (3)	0.098 (2)	−0.039 (2)	−0.0063 (16)	0.010 (2)
N1	0.0414 (9)	0.0862 (13)	0.0438 (8)	−0.0034 (8)	0.0151 (6)	0.0120 (8)
N2	0.0424 (8)	0.0710 (11)	0.0430 (7)	−0.0024 (8)	0.0095 (6)	0.0047 (7)
N3	0.0375 (8)	0.0609 (10)	0.0370 (7)	−0.0037 (7)	0.0102 (6)	0.0038 (7)
O1	0.0463 (7)	0.0976 (11)	0.0452 (6)	0.0052 (7)	0.0137 (6)	0.0196 (7)
O2	0.0552 (8)	0.1122 (13)	0.0562 (7)	−0.0142 (8)	0.0256 (6)	−0.0088 (8)
O3	0.0414 (7)	0.1015 (12)	0.0556 (7)	−0.0182 (7)	0.0100 (6)	−0.0041 (7)

Geometric parameters (Å, º) top

C1—O1	1.2251 (19)	C7—H7	0.9300
C1—N1	1.336 (2)	C8—C9	1.391 (2)
C1—N3	1.397 (2)	C8—C11	1.486 (2)
C2—N2	1.295 (2)	C9—C10	1.373 (2)
C2—N3	1.385 (2)	C9—H9	0.9300
C2—C3	1.486 (2)	C10—H10	0.9300
C3—C4	1.500 (3)	C11—O2	1.2080 (19)
C3—H3A	0.94 (2)	C11—O3	1.322 (2)
C3—H3B	0.95 (2)	C12—O3	1.460 (2)
C4—H4A	1.00 (2)	C12—C13	1.486 (4)
C4—H4B	0.93 (3)	C12—H12A	0.99 (2)
C4—H4C	1.00 (2)	C12—H12B	0.96 (2)
C5—C10	1.374 (2)	C13—H13A	0.92 (3)
C5—C6	1.389 (2)	C13—H13B	0.98 (4)
C5—N3	1.433 (2)	C13—H13C	0.96 (3)
C6—C7	1.375 (2)	N1—N2	1.376 (2)
C6—H6	0.9300	N1—H1	0.883 (19)
C7—C8	1.378 (2)

O1—C1—N1	129.64 (15)	C10—C9—C8	120.66 (16)
O1—C1—N3	127.27 (15)	C10—C9—H9	119.7
N1—C1—N3	103.09 (14)	C8—C9—H9	119.7
N2—C2—N3	110.93 (14)	C9—C10—C5	119.49 (15)
N2—C2—C3	124.44 (15)	C9—C10—H10	120.3
N3—C2—C3	124.63 (14)	C5—C10—H10	120.3
C2—C3—C4	113.30 (17)	O2—C11—O3	123.57 (16)
C2—C3—H3A	107.9 (12)	O2—C11—C8	123.62 (16)
C4—C3—H3A	109.7 (12)	O3—C11—C8	112.81 (14)
C2—C3—H3B	108.3 (12)	O3—C12—C13	106.6 (2)
C4—C3—H3B	112.2 (11)	O3—C12—H12A	106.8 (13)
H3A—C3—H3B	105.0 (17)	C13—C12—H12A	114.8 (13)
C3—C4—H4A	109.9 (12)	O3—C12—H12B	103.8 (14)
C3—C4—H4B	111.7 (15)	C13—C12—H12B	113.4 (14)
H4A—C4—H4B	107.3 (17)	H12A—C12—H12B	110 (2)
C3—C4—H4C	112.6 (13)	C12—C13—H13A	110.1 (18)
H4A—C4—H4C	106.5 (18)	C12—C13—H13B	113 (2)
H4B—C4—H4C	109 (2)	H13A—C13—H13B	110 (3)
C10—C5—C6	120.72 (15)	C12—C13—H13C	104.8 (18)
C10—C5—N3	119.11 (14)	H13A—C13—H13C	109 (2)
C6—C5—N3	120.16 (14)	H13B—C13—H13C	110 (3)
C7—C6—C5	119.14 (15)	C1—N1—N2	113.73 (14)
C7—C6—H6	120.4	C1—N1—H1	123.0 (12)
C5—C6—H6	120.4	N2—N1—H1	123.1 (12)
C6—C7—C8	120.88 (15)	C2—N2—N1	104.77 (13)
C6—C7—H7	119.6	C2—N3—C1	107.48 (13)
C8—C7—H7	119.6	C2—N3—C5	128.63 (13)
C7—C8—C9	119.07 (15)	C1—N3—C5	123.87 (13)
C7—C8—C11	118.65 (14)	C11—O3—C12	116.92 (15)
C9—C8—C11	122.26 (15)

N2—C2—C3—C4	−5.8 (3)	N3—C2—N2—N1	0.0 (2)
N3—C2—C3—C4	173.1 (2)	C3—C2—N2—N1	178.99 (19)
C10—C5—C6—C7	2.0 (3)	C1—N1—N2—C2	0.2 (2)
N3—C5—C6—C7	−178.93 (17)	N2—C2—N3—C1	−0.1 (2)
C5—C6—C7—C8	−1.0 (3)	C3—C2—N3—C1	−179.15 (19)
C6—C7—C8—C9	−0.6 (3)	N2—C2—N3—C5	178.63 (17)
C6—C7—C8—C11	177.66 (18)	C3—C2—N3—C5	−0.4 (3)
C7—C8—C9—C10	1.1 (3)	O1—C1—N3—C2	−179.77 (19)
C11—C8—C9—C10	−177.07 (19)	N1—C1—N3—C2	0.23 (19)
C8—C9—C10—C5	−0.1 (3)	O1—C1—N3—C5	1.4 (3)
C6—C5—C10—C9	−1.5 (3)	N1—C1—N3—C5	−178.60 (16)
N3—C5—C10—C9	179.42 (17)	C10—C5—N3—C2	−128.50 (19)
C7—C8—C11—O2	−2.5 (3)	C6—C5—N3—C2	52.4 (3)
C9—C8—C11—O2	175.7 (2)	C10—C5—N3—C1	50.1 (3)
C7—C8—C11—O3	177.81 (17)	C6—C5—N3—C1	−129.01 (19)
C9—C8—C11—O3	−4.0 (3)	O2—C11—O3—C12	−3.3 (3)
O1—C1—N1—N2	179.7 (2)	C8—C11—O3—C12	176.4 (2)
N3—C1—N1—N2	−0.3 (2)	C13—C12—O3—C11	179.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.883 (19)	1.94 (2)	2.808 (2)	169.5 (18)

Symmetry code: (i) −x+1, −y+2, −z.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₅N₃O₃
M_r	261.28
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	13.6111 (11), 4.0970 (2), 24.172 (2)
β (°)	100.063 (7)
V (Å³)	1327.20 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.80 × 0.41 × 0.13

Data collection
Diffractometer	Stoe IPDS 2
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8189, 2581, 1606
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.095, 0.93
No. of reflections	2581
No. of parameters	216
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.14

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.883 (19)	1.94 (2)	2.808 (2)	169.5 (18)

Symmetry code: (i) −x+1, −y+2, −z.

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer.

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