Literature DB >> 21203297

1-Phenyl-2-(1H-1,2,4-triazol-1-yl)ethanone.

Ozden Ozel Güven, Hakan Tahtacı, Simon J Coles, Tuncer Hökelek.

Abstract

In the mol-ecule of the title compound, C(10)H(9)N(3)O, the triazole and phenyl rings are nearly perpendicular to each other, with a dihedral angle of 88.72 (4)°. In the crystal structure, inter-molecular C-H⋯O and C-H⋯N hydrogen bonds link the mol-ecules. There are C-H⋯π contacts between the 1,2,4-triazole rings, and between the phenyl and 1,2,4-triazole rings, and there is a weak π-π contact between the 1,2,4-triazole and phenyl rings [centroid-to-centroid distance = 4.547 (1) Å].

Entities: Chemical Disease Species

Year: 2008 PMID： 21203297 PMCID： PMC2962216 DOI： 10.1107/S1600536808023258

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For general background, see: Holla et al. (1996 ▶); Sengupta et al. (1978 ▶); Paulvannan et al. (2001 ▶); Sui et al. (1998 ▶); Bodey (1992 ▶). For related literature, see: Caira et al. (2004 ▶); Peeters et al. (1996 ▶); Özel Güven, Tahtacı et al. (2008 ▶); Özel Güven, Erdoğan et al. (2008 ▶). For synthesis, see: Liu et al. (2006 ▶).

Experimental

Crystal data

C10H9N3O M = 187.20 Orthorhombic, a = 9.3129 (2) Å b = 8.11660 (10) Å c = 24.0475 (4) Å V = 1817.73 (5) Å3 Z = 8 Mo Kα radiation μ = 0.09 mm−1 T = 120 (2) K 0.35 × 0.2 × 0.2 mm

Data collection

Bruker Nonius KappaCCD diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.968, T max = 0.972 16799 measured reflections 2077 independent reflections 1736 reflections with I > 2σ(I) R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.060 wR(F 2) = 0.145 S = 1.17 2077 reflections 164 parameters All H-atom parameters refined Δρmax = 0.56 e Å−3 Δρmin = −0.55 e Å−3 Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; 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 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808023258/xu2439sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808023258/xu2439Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₀H₉N₃O	F₀₀₀ = 784
M_r = 187.20	D_x = 1.368 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2395 reflections
a = 9.3129 (2) Å	θ = 2.9–27.5º
b = 8.11660 (10) Å	µ = 0.09 mm⁻¹
c = 24.0475 (4) Å	T = 120 (2) K
V = 1817.73 (5) Å³	Shard, colourless
Z = 8	0.35 × 0.2 × 0.2 mm

Bruker Nonius KappaCCD diffractometer	2077 independent reflections
Radiation source: fine-focus sealed tube	1736 reflections with I > 2σ(I)
Monochromator: graphite	R_int = 0.052
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5º
T = 120(2) K	θ_min = 3.4º
φ and ω scans	h = −12→12
Absorption correction: multi-scan(SADABS; Sheldrick, 2007)	k = −10→9
T_min = 0.968, T_max = 0.972	l = −31→31
16799 measured reflections

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	All H-atom parameters refined
R[F² > 2σ(F²)] = 0.060	w = 1/[σ²(F_o²) + (0.0862P)² + 0.1878P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.145	(Δ/σ)_max < 0.001
S = 1.17	Δρ_max = 0.56 e Å⁻³
2077 reflections	Δρ_min = −0.55 e Å⁻³
164 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.141 (11)
Secondary atom site location: difference Fourier map

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.

	x	y	z	U_iso*/U_eq
O	0.27304 (10)	0.10771 (12)	0.46535 (4)	0.0301 (3)
N1	0.08642 (12)	0.25265 (13)	0.53706 (5)	0.0237 (3)
N2	0.04051 (14)	0.12395 (15)	0.56849 (5)	0.0306 (4)
N3	0.15796 (13)	0.31174 (16)	0.62134 (5)	0.0302 (3)
C1	0.08629 (16)	0.16652 (19)	0.61863 (6)	0.0302 (4)
H1	0.0645 (19)	0.097 (2)	0.6520 (7)	0.037 (4)*
C2	0.15570 (14)	0.36160 (18)	0.56884 (6)	0.0256 (3)
H2	0.1995 (17)	0.460 (2)	0.5535 (6)	0.030 (4)*
C3	0.05623 (16)	0.25908 (17)	0.47805 (5)	0.0241 (3)
H31	−0.0374 (19)	0.210 (2)	0.4711 (6)	0.032 (4)*
H32	0.0550 (18)	0.373 (2)	0.4655 (7)	0.035 (4)*
C4	0.16946 (13)	0.17185 (16)	0.44337 (5)	0.0229 (3)
C5	0.14815 (14)	0.17126 (16)	0.38202 (5)	0.0231 (3)
C6	0.25102 (16)	0.09475 (17)	0.34846 (6)	0.0284 (4)
H6	0.3339 (19)	0.048 (2)	0.3658 (7)	0.038 (5)*
C7	0.23147 (18)	0.08608 (18)	0.29144 (6)	0.0333 (4)
H7	0.3021 (18)	0.033 (2)	0.2690 (7)	0.035 (4)*
C8	0.11013 (19)	0.15544 (19)	0.26698 (6)	0.0352 (4)
H8	0.0997 (19)	0.151 (2)	0.2269 (9)	0.046 (5)*
C9	0.00879 (18)	0.23382 (18)	0.29988 (6)	0.0320 (4)
H9	−0.0794 (18)	0.281 (2)	0.2837 (7)	0.036 (4)*
C10	0.02666 (15)	0.24132 (16)	0.35721 (6)	0.0263 (4)
H10	−0.0483 (18)	0.296 (2)	0.3812 (6)	0.031 (4)*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O	0.0267 (5)	0.0372 (6)	0.0263 (5)	0.0052 (4)	−0.0022 (4)	0.0031 (4)
N1	0.0264 (6)	0.0252 (6)	0.0194 (6)	−0.0012 (4)	0.0005 (4)	0.0005 (4)
N2	0.0414 (7)	0.0283 (6)	0.0221 (6)	−0.0054 (5)	0.0016 (5)	0.0028 (5)
N3	0.0340 (7)	0.0349 (7)	0.0216 (6)	−0.0024 (5)	−0.0009 (5)	−0.0004 (5)
C1	0.0385 (8)	0.0312 (8)	0.0208 (7)	−0.0012 (6)	0.0023 (6)	0.0016 (5)
C2	0.0252 (7)	0.0295 (7)	0.0222 (7)	−0.0023 (5)	0.0005 (5)	−0.0006 (5)
C3	0.0259 (7)	0.0272 (7)	0.0191 (6)	0.0006 (5)	−0.0022 (5)	−0.0005 (5)
C4	0.0226 (6)	0.0226 (6)	0.0235 (7)	−0.0033 (5)	0.0000 (5)	0.0016 (5)
C5	0.0261 (7)	0.0221 (7)	0.0211 (7)	−0.0030 (5)	0.0002 (5)	0.0020 (5)
C6	0.0323 (7)	0.0271 (7)	0.0259 (7)	0.0009 (6)	0.0039 (6)	0.0032 (5)
C7	0.0434 (9)	0.0311 (7)	0.0256 (7)	−0.0007 (7)	0.0100 (6)	−0.0008 (6)
C8	0.0538 (10)	0.0320 (8)	0.0196 (7)	−0.0073 (7)	0.0006 (6)	0.0016 (6)
C9	0.0397 (8)	0.0306 (7)	0.0258 (7)	−0.0030 (6)	−0.0079 (6)	0.0031 (5)
C10	0.0279 (7)	0.0268 (7)	0.0242 (7)	−0.0008 (5)	−0.0018 (5)	−0.0006 (5)

O—C4	1.2170 (16)	C4—C5	1.4884 (17)
N1—N2	1.3585 (16)	C5—C6	1.398 (2)
N1—C2	1.3351 (18)	C5—C10	1.3998 (19)
N1—C3	1.4476 (16)	C6—H6	0.956 (18)
N2—C1	1.3247 (18)	C7—C6	1.3851 (19)
N3—C1	1.356 (2)	C7—H7	0.954 (18)
N3—C2	1.3258 (18)	C8—C7	1.393 (2)
C1—H1	1.001 (17)	C8—C9	1.386 (2)
C2—H2	0.972 (17)	C8—H8	0.97 (2)
C3—H31	0.974 (18)	C9—H9	0.987 (18)
C3—H32	0.973 (17)	C10—C9	1.390 (2)
C4—C3	1.5195 (18)	C10—H10	1.007 (17)

C2—N1—N2	110.05 (11)	C5—C4—C3	116.93 (11)
C2—N1—C3	129.14 (12)	C6—C5—C10	119.22 (13)
N2—N1—C3	120.80 (11)	C6—C5—C4	118.82 (12)
C1—N2—N1	101.81 (11)	C10—C5—C4	121.93 (12)
C2—N3—C1	102.23 (11)	C7—C6—C5	120.26 (14)
N2—C1—N3	115.39 (12)	C7—C6—H6	121.1 (10)
N2—C1—H1	121.1 (10)	C5—C6—H6	118.6 (10)
N3—C1—H1	123.4 (10)	C6—C7—C8	120.28 (14)
N3—C2—N1	110.53 (13)	C6—C7—H7	119.5 (10)
N3—C2—H2	127.4 (9)	C8—C7—H7	120.2 (10)
N1—C2—H2	122.1 (9)	C9—C8—C7	119.79 (13)
N1—C3—C4	112.73 (11)	C9—C8—H8	121.0 (11)
N1—C3—H31	109.1 (9)	C7—C8—H8	119.2 (11)
C4—C3—H31	109.5 (10)	C8—C9—C10	120.31 (14)
N1—C3—H32	109.9 (10)	C8—C9—H9	121.3 (10)
C4—C3—H32	106.3 (10)	C10—C9—H9	118.3 (10)
H31—C3—H32	109.2 (14)	C9—C10—C5	120.11 (13)
O—C4—C5	122.34 (12)	C9—C10—H10	120.4 (9)
O—C4—C3	120.73 (12)	C5—C10—H10	119.5 (9)

C2—N1—N2—C1	0.33 (15)	C3—C4—C5—C6	178.95 (12)
C3—N1—N2—C1	−178.72 (12)	O—C4—C5—C10	178.18 (12)
N2—N1—C2—N3	−0.35 (16)	C3—C4—C5—C10	−2.67 (18)
C3—N1—C2—N3	178.60 (12)	C10—C5—C6—C7	−1.1 (2)
C2—N1—C3—C4	93.49 (16)	C4—C5—C6—C7	177.33 (12)
N2—N1—C3—C4	−87.66 (15)	C6—C5—C10—C9	0.3 (2)
N1—N2—C1—N3	−0.21 (17)	C4—C5—C10—C9	−178.08 (12)
C2—N3—C1—N2	0.01 (17)	C8—C7—C6—C5	0.9 (2)
C1—N3—C2—N1	0.20 (15)	C9—C8—C7—C6	0.2 (2)
O—C4—C3—N1	−0.91 (18)	C7—C8—C9—C10	−1.0 (2)
C5—C4—C3—N1	179.92 (11)	C5—C10—C9—C8	0.7 (2)
O—C4—C5—C6	−0.21 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Oⁱ	0.970 (16)	2.449 (15)	3.2595 (17)	140.9 (12)
C3—H32···Oⁱ	0.973 (16)	2.489 (16)	3.2601 (17)	136.1 (13)
C8—H8···N3ⁱⁱ	0.97 (2)	2.61 (2)	3.5405 (19)	160.2 (14)
C1—H1···Cg2ⁱⁱⁱ	1.001 (17)	2.840 (18)	3.620 (2)	135.20 (13)
C2—H2···Cg1^iv	0.972 (17)	3.013 (16)	3.829 (2)	142.42 (12)

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the rings N1–N3/C1/C2 and C5–C10, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯Oⁱ	0.970 (16)	2.449 (15)	3.2595 (17)	140.9 (12)
C3—H32⋯Oⁱ	0.973 (16)	2.489 (16)	3.2601 (17)	136.1 (13)
C8—H8⋯N3ⁱⁱ	0.97 (2)	2.61 (2)	3.5405 (19)	160.2 (14)
C1—H1⋯Cg2ⁱⁱⁱ	1.001 (17)	2.840 (18)	3.620 (2)	135.20 (13)
C2—H2⋯Cg1^iv	0.972 (17)	3.013 (16)	3.829 (2)	142.42 (12)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

7 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

2. Synthesis, characterisation and antifungal activity of some N-bridged heterocycles derived from 3-(3-bromo-4-methoxyphenyl)-4-amino-5-mercapto-1,2,4-triazole.

Authors: B S Holla; K N Poojary; B Kalluraya; P V Gowda
Journal: Farmaco Date: 1996-12

3. 2-(1H-Benzimidazol-1-yl)-1-phenyl-ethanone.

Authors: Ozden Ozel Güven; Taner Erdoğan; Simon J Coles; Tuncer Hökelek
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2008-06-28

4. SAR studies of diaryltriazoles against bacterial two-component regulatory systems and their antibacterial activities.

Authors: Z Sui; J Guan; D J Hlasta; M J Macielag; B D Foleno; R M Goldschmidt; M J Loeloff; G C Webb; J F Barrett
Journal: Bioorg Med Chem Lett Date: 1998-07-21 Impact factor: 2.823

5. Preparation and crystal characterization of a polymorph, a monohydrate, and an ethyl acetate solvate of the antifungal fluconazole.

Authors: Mino R Caira; Khouloud A Alkhamis; Rana M Obaidat
Journal: J Pharm Sci Date: 2004-03 Impact factor: 3.534

Review 6. Azole antifungal agents.

Authors: G P Bodey
Journal: Clin Infect Dis Date: 1992-03 Impact factor: 9.079

7. 1-Phenyl-2-(1H-1,2,4-triazol-1-yl)ethanol.

Authors: Ozden Ozel Güven; Hakan Tahtacı; Simon J Coles; Tuncer Hökelek
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2008-06-13

7 in total

2 in total

1. 2-(2H-Indazol-2-yl)-1-phenyl-ethanone.

Authors: Ozden Ozel Güven; Gökhan Türk; Philip D F Adler; Simon J Coles; Tuncer Hökelek
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2013-01-04

2. 1-(Furan-2-yl)-2-(2H-indazol-2-yl)ethanone.

Authors: Ozden Ozel Güven; Gökhan Türk; Philip D F Adler; Simon J Coles; Tuncer Hökelek
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2014-03-29

2 in total