3-(2H-Benzotriazol-2-yl)-1-(4-fluoro­phen­yl)propan-1-one

Pan, Z.-F.

doi:10.1107/S1600536810013917

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 5| May 2010| Page o1124

https://doi.org/10.1107/S1600536810013917

Open

access

3-(2H-Benzotriazol-2-yl)-1-(4-fluorophenyl)propan-1-one

Zhi-Fang Pan ^a ^*

^aWeifang Medical University, Weifang 261042, People's Republic of China
^*Correspondence e-mail: Weichidu@163.com

(Received 12 April 2010; accepted 15 April 2010; online 21 April 2010)

In the title compound, C₁₅H₁₂FN₃O, the benzotriazole ring system is essentially planar, with a maximum deviation from the least-squares plane of 0.016 (3) Å. The dihedral angle between this ring system and the fluoro-substituted benzene ring is 67.97 (2)°. The crystal structure is stabilized by weak intermolecular C—H⋯N interactions.

Related literature

For applications of benzotriazole derivatives, see: Chen & Wu (2005 ). For standard bond distances, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₅H₁₂FN₃O
M_r = 269.28
Monoclinic, P 2₁
a = 5.7858 (12) Å
b = 5.6814 (11) Å
c = 19.313 (4) Å
β = 90.77 (3)°
V = 634.8 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.20 × 0.18 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer
3943 measured reflections
1240 independent reflections
1122 reflections with I > 2σ(I)
R_int = 0.135

Refinement

R[F² > 2σ(F²)] = 0.081
wR(F²) = 0.210
S = 1.07
1240 reflections
181 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.30 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
C14—H14B⋯N1ⁱ	0.97	2.58	3.511 (3)	161
Symmetry code: (i) x-1, y, z.

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810013917/lh5027sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810013917/lh5027Isup2.hkl

checkCIF report

Comment top

1H-Benzotriazole and its derivatives are an important class of compounds because they exhibit a broad spectrum of pharmacological activities such as antifungal, antitumor and antineoplastic activities (Chen & Wu., 2005). 1H and 2H-Benzotriazole are tautomers. We report here the synthesis and structure of the title compound, (I) (Fig. 1), as part of our ongoing studies on new benzotriazole compounds with potential bioactivity. All bond lengths (Allen et al., 1987) and angles in (I) are within normal ranges. The benzotriazole ring system is essentially planar with a maximum deviation from the least squares plane of 0.016 (3)Å. The dihedral angle between this ring system and the fluro substituted benzene ring is 67.97 (2). The crystal structure is stabilized by weak intermolecular C—H···N interactions.

Related literature top

For applications of benzotriazole derivatives, see: Chen & Wu (2005). For standard bond distances, see: Allen et al. (1987).

Experimental top

To a solution of 1-(4-ethylphenyl)-3-(dimethylamino)propan-1-one (12.05 g, 0.05 mol) in water (25 ml) was added benzotriazole (7.1 g, 0.06 mol). The mixture was heated under reflux for 5 h. The solution was filtered,concentrated and purified by flash chromatography (silica gel,using petroleum ether-ethylacetate(4:1 v/v). to afford the title compound. Colourless single crystals suitable for X-ray diffraction study were obtained by slow evaporation of a ethanol solution over a period of 5 d.

Structure description top

For applications of benzotriazole derivatives, see: Chen & Wu (2005). For standard bond distances, see: Allen et al. (1987).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), drawn with 30% probability ellipsoids.
	Fig. 2. Part of the crystal structure of (I) showing hydrogen bonds as dashed lines.

3-(2H-Benzotriazol-2-yl)-1-(4-fluorophenyl)propan-1-one top

Crystal data top

C₁₅H₁₂FN₃O	F(000) = 280
M_r = 269.28	D_x = 1.409 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1874 reflections
a = 5.7858 (12) Å	θ = 1.1–25.0°
b = 5.6814 (11) Å	µ = 0.10 mm⁻¹
c = 19.313 (4) Å	T = 293 K
β = 90.77 (3)°	Block, colorless
V = 634.8 (2) Å³	0.20 × 0.18 × 0.10 mm
Z = 2

Data collection top

Bruker SMART CCD diffractometer	1122 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.135
Graphite monochromator	θ_max = 25.0°, θ_min = 1.1°
φ and ω scans	h = −6→6
3943 measured reflections	k = −6→6
1240 independent reflections	l = −22→20

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)] = 0.081	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.210	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.1432P)² + 0.1388P] where P = (F_o² + 2F_c²)/3
1240 reflections	(Δ/σ)_max = 0.002
181 parameters	Δρ_max = 0.30 e Å⁻³
1 restraint	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₁₅H₁₂FN₃O	V = 634.8 (2) Å³
M_r = 269.28	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 5.7858 (12) Å	µ = 0.10 mm⁻¹
b = 5.6814 (11) Å	T = 293 K
c = 19.313 (4) Å	0.20 × 0.18 × 0.10 mm
β = 90.77 (3)°

Data collection top

Bruker SMART CCD diffractometer	1122 reflections with I > 2σ(I)
3943 measured reflections	R_int = 0.135
1240 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.081	1 restraint
wR(F²) = 0.210	H-atom parameters constrained
S = 1.07	Δρ_max = 0.30 e Å⁻³
1240 reflections	Δρ_min = −0.34 e Å⁻³
181 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 > 2sigma(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
F	0.0574 (7)	1.0117 (7)	0.01386 (19)	0.0505 (11)
O	0.9115 (8)	1.3049 (7)	0.1980 (2)	0.0434 (12)
N1	1.3671 (7)	0.6871 (8)	0.3093 (2)	0.0278 (10)
N2	1.0658 (8)	0.6958 (8)	0.3810 (2)	0.0300 (10)
N3	1.1720 (8)	0.7892 (8)	0.3293 (2)	0.0265 (10)
C9	1.3499 (10)	0.1759 (10)	0.4572 (3)	0.0316 (13)
H9A	1.3402	0.0609	0.4913	0.038*
C15	0.8110 (10)	1.1189 (10)	0.1966 (3)	0.0300 (13)
C14	0.8827 (10)	0.9205 (9)	0.2440 (3)	0.0292 (12)
H14A	0.9270	0.7856	0.2164	0.035*
H14B	0.7524	0.8746	0.2720	0.035*
C12	1.3905 (9)	0.5068 (10)	0.3556 (3)	0.0274 (12)
C5	0.6140 (11)	1.0790 (10)	0.1461 (3)	0.0326 (13)
C13	1.0823 (9)	0.9904 (10)	0.2907 (3)	0.0293 (12)
H13A	1.2047	1.0571	0.2630	0.035*
H13B	1.0315	1.1103	0.3229	0.035*
C11	1.2016 (9)	0.5119 (10)	0.4001 (3)	0.0276 (12)
C2	0.2439 (10)	1.0338 (10)	0.0570 (3)	0.0344 (14)
C6	0.5609 (10)	1.2550 (10)	0.0984 (3)	0.0315 (13)
H6A	0.6528	1.3891	0.0966	0.038*
C10	1.1818 (10)	0.3418 (10)	0.4533 (3)	0.0285 (12)
H10A	1.0595	0.3438	0.4841	0.034*
C8	1.5400 (10)	0.1698 (10)	0.4116 (3)	0.0336 (13)
H8A	1.6498	0.0512	0.4164	0.040*
C3	0.2883 (12)	0.8551 (12)	0.1038 (3)	0.0416 (15)
H3A	0.1945	0.7223	0.1050	0.050*
C4	0.4757 (11)	0.8775 (10)	0.1490 (3)	0.0356 (14)
H4A	0.5090	0.7594	0.1809	0.043*
C7	1.5654 (10)	0.3346 (10)	0.3607 (3)	0.0309 (12)
H7A	1.6910	0.3332	0.3311	0.037*
C1	0.3754 (11)	1.2338 (10)	0.0540 (3)	0.0376 (15)
H1B	0.3395	1.3526	0.0226	0.045*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F	0.048 (2)	0.046 (2)	0.057 (2)	0.0034 (19)	−0.0271 (17)	−0.0036 (19)
O	0.048 (3)	0.026 (2)	0.056 (3)	−0.007 (2)	−0.019 (2)	0.006 (2)
N1	0.027 (2)	0.025 (2)	0.031 (3)	0.001 (2)	−0.0019 (17)	0.0008 (19)
N2	0.027 (2)	0.021 (2)	0.042 (3)	−0.001 (2)	−0.0053 (18)	−0.002 (2)
N3	0.028 (2)	0.020 (2)	0.032 (3)	0.0000 (18)	−0.0043 (18)	−0.0002 (19)
C9	0.040 (3)	0.025 (3)	0.029 (3)	−0.010 (3)	−0.012 (2)	0.006 (2)
C15	0.030 (3)	0.022 (3)	0.037 (3)	0.001 (2)	−0.004 (2)	−0.004 (2)
C14	0.033 (3)	0.023 (3)	0.032 (3)	0.001 (2)	0.000 (2)	−0.002 (2)
C12	0.030 (3)	0.020 (2)	0.032 (3)	−0.002 (2)	−0.010 (2)	0.004 (2)
C5	0.038 (3)	0.025 (3)	0.035 (3)	0.002 (2)	−0.004 (2)	−0.005 (2)
C13	0.028 (3)	0.020 (2)	0.040 (3)	0.000 (2)	−0.011 (2)	−0.001 (2)
C11	0.028 (3)	0.021 (2)	0.034 (3)	−0.011 (2)	−0.009 (2)	0.002 (2)
C2	0.032 (3)	0.039 (3)	0.031 (3)	0.011 (3)	−0.008 (2)	−0.007 (3)
C6	0.035 (3)	0.026 (3)	0.034 (3)	0.004 (2)	−0.005 (2)	0.006 (2)
C10	0.032 (3)	0.027 (3)	0.026 (3)	−0.008 (2)	−0.0030 (19)	−0.001 (2)
C8	0.036 (3)	0.027 (3)	0.038 (3)	−0.004 (2)	−0.012 (2)	0.001 (3)
C3	0.044 (4)	0.030 (3)	0.050 (4)	−0.007 (3)	−0.010 (3)	−0.002 (3)
C4	0.042 (3)	0.030 (3)	0.035 (3)	−0.003 (3)	−0.007 (2)	−0.001 (3)
C7	0.028 (3)	0.024 (3)	0.040 (3)	0.000 (2)	−0.009 (2)	−0.006 (2)
C1	0.043 (4)	0.025 (3)	0.044 (4)	0.010 (3)	−0.010 (3)	0.009 (2)

Geometric parameters (Å, º) top

F—C2	1.360 (7)	C5—C6	1.390 (8)
O—C15	1.207 (7)	C5—C4	1.399 (9)
N1—N3	1.331 (7)	C13—H13A	0.9700
N1—C12	1.364 (7)	C13—H13B	0.9700
N2—N3	1.293 (7)	C11—C10	1.416 (8)
N2—C11	1.356 (7)	C2—C1	1.369 (9)
N3—C13	1.457 (7)	C2—C3	1.381 (9)
C9—C10	1.356 (8)	C6—C1	1.370 (9)
C9—C8	1.419 (9)	C6—H6A	0.9300
C9—H9A	0.9300	C10—H10A	0.9300
C15—C14	1.506 (7)	C8—C7	1.367 (9)
C15—C5	1.508 (7)	C8—H8A	0.9300
C14—C13	1.510 (7)	C3—C4	1.388 (9)
C14—H14A	0.9700	C3—H3A	0.9300
C14—H14B	0.9700	C4—H4A	0.9300
C12—C11	1.400 (8)	C7—H7A	0.9300
C12—C7	1.410 (8)	C1—H1B	0.9300

N3—N1—C12	102.4 (4)	H13A—C13—H13B	108.0
N3—N2—C11	104.3 (5)	N2—C11—C12	107.7 (5)
N2—N3—N1	117.3 (4)	N2—C11—C10	132.1 (5)
N2—N3—C13	123.2 (5)	C12—C11—C10	120.2 (5)
N1—N3—C13	119.4 (5)	F—C2—C1	119.2 (5)
C10—C9—C8	122.9 (5)	F—C2—C3	118.2 (5)
C10—C9—H9A	118.5	C1—C2—C3	122.6 (5)
C8—C9—H9A	118.5	C1—C6—C5	121.0 (5)
O—C15—C14	120.9 (5)	C1—C6—H6A	119.5
O—C15—C5	120.4 (5)	C5—C6—H6A	119.5
C14—C15—C5	118.7 (5)	C9—C10—C11	116.7 (5)
C15—C14—C13	111.6 (5)	C9—C10—H10A	121.6
C15—C14—H14A	109.3	C11—C10—H10A	121.6
C13—C14—H14A	109.3	C7—C8—C9	121.5 (5)
C15—C14—H14B	109.3	C7—C8—H8A	119.3
C13—C14—H14B	109.3	C9—C8—H8A	119.3
H14A—C14—H14B	108.0	C4—C3—C2	118.7 (6)
N1—C12—C11	108.4 (5)	C4—C3—H3A	120.6
N1—C12—C7	129.2 (5)	C2—C3—H3A	120.6
C11—C12—C7	122.4 (5)	C3—C4—C5	119.5 (6)
C6—C5—C4	119.6 (5)	C3—C4—H4A	120.2
C6—C5—C15	118.6 (5)	C5—C4—H4A	120.2
C4—C5—C15	121.7 (5)	C8—C7—C12	116.2 (6)
N3—C13—C14	111.3 (5)	C8—C7—H7A	121.9
N3—C13—H13A	109.4	C12—C7—H7A	121.9
C14—C13—H13A	109.4	C2—C1—C6	118.6 (5)
N3—C13—H13B	109.4	C2—C1—H1B	120.7
C14—C13—H13B	109.4	C6—C1—H1B	120.7

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14B···N1ⁱ	0.97	2.58	3.511 (3)	161

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₂FN₃O
M_r	269.28
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	5.7858 (12), 5.6814 (11), 19.313 (4)
β (°)	90.77 (3)
V (Å³)	634.8 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.20 × 0.18 × 0.10

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3943, 1240, 1122
R_int	0.135
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.081, 0.210, 1.07
No. of reflections	1240
No. of parameters	181
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.34

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14B···N1ⁱ	0.97	2.58	3.511 (3)	161

Symmetry code: (i) x−1, y, z.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, Z.-Y. & Wu, M.-J. (2005). Org. Lett. 7, 475–477. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals 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.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 5| May 2010| Page o1124

https://doi.org/10.1107/S1600536810013917

Open

access