(2,4-Difluoro­phen­yl)[1-(1H-1,2,4-triazol-1-yl)cyclo­prop­yl]methanone

Wu, C.; Lei, W.; Ma, H.; Qiao, J.; Li, A.

doi:10.1107/S1600536811040037

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o2913

doi:10.1107/S1600536811040037

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(2,4-Difluorophenyl)[1-(1H-1,2,4-triazol-1-yl)cyclopropyl]methanone

Chunli Wu,^a ^* Wei Lei,^a Huiyan Ma,^a Jiabin Qiao ^a and Aixing Li ^a

^aSchool of Pharmaceutical Sciences, Zhengzhou Univresity, Zhengzhou 450001, People's Republic of China
^*Correspondence e-mail: kedi2009@126.com

(Received 17 September 2011; accepted 29 September 2011; online 12 October 2011)

The asymmetric unit of the title compound, C₁₂H₉F₂N₃O, contains two independent molecules (A and B) in which the benzene and cyclopropane rings form dihedral angles of 33.0 (1) and 29.7 (1)°, respectively. In the crystal, weak intermolecular C—H⋯O hydrogen bonds link alternating A and B molecules into chains along [010].

Related literature

For applications of triazole derivatives, see: Che & Zhang (2009 ); Lieven & Leo (2005 ). For related structures, see: Tarun et al. (1998 ).

Experimental

Crystal data

C₁₂H₉F₂N₃O
M_r = 249.22
Triclinic, $[P \overline 1]$
a = 9.6067 (11) Å
b = 11.4840 (13) Å
c = 11.9127 (14) Å
α = 73.652 (1)°
β = 84.202 (2)°
γ = 69.260 (1)°
V = 1179.4 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 298 K
0.49 × 0.40 × 0.38 mm

Data collection

Rigaku R-AXIS CCD detector diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.983, T_max = 0.986
5900 measured reflections
4080 independent reflections
2816 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.111
S = 1.02
4080 reflections
326 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12A⋯O2ⁱ	0.93	2.35	3.268 (2)	171
C24—H24A⋯O1ⁱⁱ	0.93	2.37	3.265 (3)	161
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) -x+1, -y+1, -z+1.

Data collection: R-AXIS II Software (Rigaku, 1997 ); cell refinement: R-AXIS II Software; data reduction: R-AXIS II Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: TEXSAN (Molecular Structure Corporation, 1992 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811040037/cv5156sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811040037/cv5156Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811040037/cv5156Isup3.cml

checkCIF report

Comment top

The triazole derivatives exhibit various antifungal activities (Che & Zhang, 2009; Lieven &Leo, 2005). As our contribution to the research of triazole compounds, herewith we report the crystal structure of the title compound (I).

The asymmetric unit of (I) contains two independent molecules, A and B, respectively (Fig. 1). The benzene and cyclopropane rings form a dihedral angle of 33.0 (1)° in A and 29.7 (1)° in B. All bond lengths and angles in (I) are normal and comparable with those found in related compounds (Tarun et al., 1998). In the crystal structure, weak intermolecular C—H···O hydrogen bonds (Table 1) link alternating A and B molecules into chains in [010].

Related literature top

For applications of triazole derivatives, see: Che & Zhang (2009); Lieven & Leo (2005). For related structures, see: Tarun et al. (1998).

Experimental top

To a suspension of 2.27 g (10 mmol) of 2-(1H-1,2,4- triazol)-2',4'-difluoroacetophenone and 1.68 g (30 mmol) of KOH in 60 ml of stirred acetone, was cautiously added 2.6 ml (30 mmol) of 1,2-dibromoethane. After the mixture was stirred at room temperature for 6 hr, the mixture was filtered,and then solvent was evaporated. The crystalline product was separated by chromatographic column(petroleum ether:acetone 6:1) with yield 30%. Crystals suitable for X-ray analysis were grown by slow evaporation from acetone at room temperature for two weeks. M.p. 89–90 °C. Spectroscopic analysis: ¹H NMR (400 MHz, CDCl₃) σ: 8.21(s, 1H), 7.80(s, 1H), 7.40(1H, dd, J=14.5 8.2 Hz), 6.87(m, 1H), 6.73(m, 1H), 2.13(1H, q, J=5.0 Hz), 1.80(1H, q, J=5.0 Hz). ¹³C NMR (100 MHz, CDCl₃) σ: 196.47, 165.45, 165.33, 162.95, 162.83, 160.62, 160.50, 158.12, 157.99, 152.33, 146.44, 130.94, 130.89, 130.83, 130.79, 122.71, 122.67, 122.55, 122.51, 112.48, 112.44, 112.26, 112.23, 105.25, 104.99, 104.73, 49.23, 19.04.

Computing details top

Data collection: R-AXIS II Software (Rigaku, 1997); cell refinement: R-AXIS II Software (Rigaku, 1997); data reduction: R-AXIS II Software (Rigaku, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: TEXSAN (Molecular Structure Corporation, 1992); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. Two independent molecules of (I) showing the atomic numbering and 30% probability displacement ellipsoids.

(2,4-Difluorophenyl)[1-(1H-1,2,4-triazol-1-yl)cyclopropyl]methanone top

Crystal data top

C₁₂H₉F₂N₃O	F(000) = 512
M_r = 249.22	D_x = 1.404 Mg m⁻³
Triclinic, P1	Melting point: 362.15 K
a = 9.6067 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.4840 (13) Å	Cell parameters from 2449 reflections
c = 11.9127 (14) Å	θ = 4.9–52.5°
α = 73.652 (1)°	µ = 0.12 mm⁻¹
β = 84.202 (2)°	T = 298 K
γ = 69.260 (1)°	Block, colourless
V = 1179.4 (2) Å³	0.49 × 0.40 × 0.38 mm
Z = 4

Data collection top

Rigaku R-AXIS CCD detector diffractometer	4080 independent reflections
Radiation source: fine-focus sealed tube	2816 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.4°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→11
T_min = 0.983, T_max = 0.986	k = −13→12
5900 measured reflections	l = −13→14

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.038	H-atom parameters constrained
wR(F²) = 0.111	w = 1/[σ²(F_o²) + (0.0469P)² + 0.2296P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
4080 reflections	Δρ_max = 0.14 e Å⁻³
326 parameters	Δρ_min = −0.16 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0200 (19)

Crystal data top

C₁₂H₉F₂N₃O	γ = 69.260 (1)°
M_r = 249.22	V = 1179.4 (2) Å³
Triclinic, P1	Z = 4
a = 9.6067 (11) Å	Mo Kα radiation
b = 11.4840 (13) Å	µ = 0.12 mm⁻¹
c = 11.9127 (14) Å	T = 298 K
α = 73.652 (1)°	0.49 × 0.40 × 0.38 mm
β = 84.202 (2)°

Data collection top

Rigaku R-AXIS CCD detector diffractometer	4080 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2816 reflections with I > 2σ(I)
T_min = 0.983, T_max = 0.986	R_int = 0.017
5900 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.111	H-atom parameters constrained
S = 1.02	Δρ_max = 0.14 e Å⁻³
4080 reflections	Δρ_min = −0.16 e Å⁻³
326 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
F1	1.40947 (15)	0.64219 (16)	0.00685 (15)	0.1017 (5)
F2	0.96387 (13)	0.81942 (11)	0.18986 (12)	0.0717 (4)
F3	0.93617 (18)	0.62666 (18)	0.51796 (17)	0.1195 (6)
F4	0.49568 (16)	0.58407 (11)	0.69708 (13)	0.0857 (4)
C1	1.2783 (2)	0.6334 (2)	0.0552 (2)	0.0647 (6)
C2	1.2443 (2)	0.5265 (2)	0.0588 (2)	0.0668 (6)
H2A	1.3102	0.4597	0.0302	0.080*
C3	1.1099 (2)	0.52091 (19)	0.10591 (18)	0.0584 (5)
H3A	1.0851	0.4485	0.1102	0.070*
C4	1.0094 (2)	0.62149 (17)	0.14757 (16)	0.0478 (5)
C5	1.0544 (2)	0.72398 (18)	0.14347 (17)	0.0512 (5)
C6	1.1876 (2)	0.7330 (2)	0.09827 (18)	0.0591 (6)
H6A	1.2151	0.8033	0.0969	0.071*
C7	0.8640 (2)	0.61067 (19)	0.19488 (18)	0.0556 (5)
C8	0.7238 (2)	0.72473 (17)	0.16397 (16)	0.0463 (5)
C9	0.5788 (2)	0.7042 (2)	0.1994 (2)	0.0678 (6)
H9A	0.4949	0.7541	0.1470	0.081*
H9B	0.5817	0.6175	0.2403	0.081*
C10	0.6327 (3)	0.7735 (2)	0.26206 (19)	0.0700 (6)
H10A	0.6689	0.7291	0.3413	0.084*
H10B	0.5820	0.8658	0.2480	0.084*
N2	0.7482 (2)	0.78048 (16)	−0.04611 (14)	0.0591 (5)
N3	0.7144 (2)	0.99200 (16)	−0.08345 (15)	0.0647 (5)
C13	0.8010 (3)	0.6783 (3)	0.5629 (2)	0.0762 (7)
C14	0.7534 (3)	0.8061 (2)	0.5600 (2)	0.0788 (7)
H14A	0.8135	0.8558	0.5296	0.095*
C15	0.6152 (3)	0.8589 (2)	0.6032 (2)	0.0691 (7)
H15A	0.5821	0.9455	0.6030	0.083*
C16	0.5225 (2)	0.78710 (18)	0.64746 (18)	0.0573 (6)
C17	0.5794 (3)	0.65813 (19)	0.64870 (19)	0.0604 (6)
C18	0.7182 (3)	0.6007 (2)	0.6075 (2)	0.0690 (6)
H18A	0.7540	0.5134	0.6100	0.083*
C19	0.3729 (3)	0.8500 (2)	0.69230 (19)	0.0678 (6)
C20	0.2382 (2)	0.83360 (19)	0.65607 (17)	0.0582 (5)
C21	0.1380 (3)	0.7875 (3)	0.7494 (2)	0.0928 (9)
H21A	0.0900	0.7320	0.7342	0.111*
H21B	0.1660	0.7684	0.8303	0.111*
C22	0.0889 (3)	0.9228 (3)	0.6814 (2)	0.0884 (8)
H22A	0.0864	0.9871	0.7204	0.106*
H22B	0.0105	0.9507	0.6244	0.106*
N6	0.2577 (2)	0.69776 (17)	0.41577 (15)	0.0633 (5)
N5	0.26550 (18)	0.87964 (14)	0.44550 (14)	0.0533 (4)
C12	0.7074 (2)	0.94269 (18)	0.02927 (17)	0.0536 (5)
H12A	0.6907	0.9894	0.0846	0.064*
C11	0.7406 (3)	0.8883 (2)	−0.12474 (18)	0.0662 (6)
H11A	0.7525	0.8930	−0.2042	0.079*
N1	0.72688 (16)	0.81780 (13)	0.05495 (12)	0.0423 (4)
N4	0.25081 (17)	0.79612 (14)	0.54907 (13)	0.0464 (4)
C24	0.2467 (2)	0.68990 (19)	0.52741 (19)	0.0588 (5)
H24A	0.2371	0.6190	0.5847	0.071*
C23	0.2694 (2)	0.81488 (19)	0.37037 (18)	0.0542 (5)
H23A	0.2797	0.8479	0.2904	0.065*
O1	0.85746 (19)	0.50900 (16)	0.25590 (17)	0.0984 (6)
O2	0.3590 (2)	0.9191 (2)	0.75643 (18)	0.1132 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0625 (9)	0.1236 (13)	0.1359 (14)	−0.0376 (9)	0.0205 (9)	−0.0597 (11)
F2	0.0660 (8)	0.0637 (8)	0.0980 (10)	−0.0180 (6)	−0.0012 (7)	−0.0458 (7)
F3	0.0818 (12)	0.1246 (14)	0.1586 (17)	−0.0256 (10)	−0.0010 (10)	−0.0595 (13)
F4	0.1023 (11)	0.0479 (7)	0.1065 (11)	−0.0320 (7)	−0.0159 (8)	−0.0061 (7)
C1	0.0459 (12)	0.0778 (16)	0.0745 (15)	−0.0183 (11)	−0.0014 (10)	−0.0297 (13)
C2	0.0566 (14)	0.0630 (14)	0.0824 (16)	−0.0086 (11)	−0.0069 (11)	−0.0345 (12)
C3	0.0601 (13)	0.0419 (11)	0.0718 (14)	−0.0118 (10)	−0.0159 (11)	−0.0146 (10)
C4	0.0504 (11)	0.0401 (10)	0.0495 (11)	−0.0122 (9)	−0.0116 (9)	−0.0065 (8)
C5	0.0519 (12)	0.0468 (11)	0.0566 (12)	−0.0101 (9)	−0.0101 (9)	−0.0215 (9)
C6	0.0542 (13)	0.0580 (13)	0.0741 (15)	−0.0230 (10)	−0.0108 (11)	−0.0225 (11)
C7	0.0643 (13)	0.0430 (12)	0.0546 (12)	−0.0207 (10)	−0.0066 (10)	−0.0001 (9)
C8	0.0522 (11)	0.0431 (11)	0.0444 (11)	−0.0203 (9)	−0.0006 (9)	−0.0075 (8)
C9	0.0594 (13)	0.0629 (14)	0.0797 (16)	−0.0295 (11)	0.0040 (11)	−0.0068 (12)
C10	0.0797 (16)	0.0751 (15)	0.0522 (13)	−0.0272 (13)	0.0119 (11)	−0.0155 (11)
N2	0.0828 (13)	0.0495 (10)	0.0472 (10)	−0.0189 (9)	−0.0041 (8)	−0.0197 (8)
N3	0.0933 (14)	0.0466 (10)	0.0496 (11)	−0.0238 (9)	−0.0031 (9)	−0.0048 (8)
C13	0.0669 (16)	0.0743 (17)	0.0896 (18)	−0.0180 (14)	−0.0208 (13)	−0.0258 (14)
C14	0.0871 (19)	0.0678 (16)	0.0901 (18)	−0.0367 (15)	−0.0249 (15)	−0.0121 (14)
C15	0.0893 (18)	0.0437 (12)	0.0798 (16)	−0.0221 (12)	−0.0336 (14)	−0.0140 (11)
C16	0.0774 (15)	0.0406 (11)	0.0577 (13)	−0.0164 (10)	−0.0262 (11)	−0.0146 (9)
C17	0.0800 (16)	0.0407 (11)	0.0635 (14)	−0.0227 (11)	−0.0236 (11)	−0.0075 (10)
C18	0.0771 (16)	0.0447 (12)	0.0835 (16)	−0.0082 (12)	−0.0308 (13)	−0.0198 (11)
C19	0.0935 (18)	0.0516 (13)	0.0608 (14)	−0.0151 (12)	−0.0176 (12)	−0.0253 (11)
C20	0.0743 (14)	0.0527 (12)	0.0469 (12)	−0.0143 (11)	−0.0016 (10)	−0.0210 (10)
C21	0.117 (2)	0.112 (2)	0.0538 (15)	−0.0430 (19)	0.0201 (14)	−0.0304 (15)
C22	0.0852 (18)	0.094 (2)	0.0825 (18)	−0.0074 (15)	0.0070 (14)	−0.0493 (16)
N6	0.0885 (13)	0.0544 (11)	0.0570 (11)	−0.0311 (10)	0.0008 (9)	−0.0215 (9)
N5	0.0702 (11)	0.0415 (9)	0.0490 (10)	−0.0234 (8)	0.0010 (8)	−0.0078 (8)
C12	0.0735 (14)	0.0383 (11)	0.0507 (12)	−0.0181 (10)	−0.0012 (10)	−0.0151 (9)
C11	0.0932 (17)	0.0598 (14)	0.0409 (12)	−0.0215 (12)	−0.0025 (11)	−0.0111 (11)
N1	0.0511 (9)	0.0361 (8)	0.0403 (8)	−0.0138 (7)	−0.0024 (7)	−0.0117 (7)
N4	0.0597 (10)	0.0391 (8)	0.0428 (9)	−0.0187 (7)	−0.0004 (7)	−0.0121 (7)
C24	0.0857 (15)	0.0456 (12)	0.0534 (13)	−0.0350 (11)	0.0014 (10)	−0.0105 (9)
C23	0.0663 (13)	0.0528 (12)	0.0447 (11)	−0.0221 (10)	0.0050 (9)	−0.0140 (9)
O1	0.0834 (12)	0.0565 (10)	0.1217 (15)	−0.0247 (9)	−0.0031 (10)	0.0301 (10)
O2	0.1266 (16)	0.1143 (15)	0.1246 (16)	−0.0233 (12)	−0.0190 (12)	−0.0879 (14)

Geometric parameters (Å, º) top

F1—C1	1.357 (3)	C13—C14	1.365 (3)
F2—C5	1.354 (2)	C14—C15	1.364 (3)
F3—C13	1.348 (3)	C14—H14A	0.9300
F4—C17	1.348 (2)	C15—C16	1.390 (3)
C1—C6	1.366 (3)	C15—H15A	0.9300
C1—C2	1.366 (3)	C16—C17	1.382 (3)
C2—C3	1.371 (3)	C16—C19	1.483 (3)
C2—H2A	0.9300	C17—C18	1.371 (3)
C3—C4	1.396 (3)	C18—H18A	0.9300
C3—H3A	0.9300	C19—O2	1.215 (2)
C4—C5	1.378 (3)	C19—C20	1.493 (3)
C4—C7	1.486 (3)	C20—N4	1.437 (2)
C5—C6	1.364 (3)	C20—C22	1.498 (3)
C6—H6A	0.9300	C20—C21	1.502 (3)
C7—O1	1.209 (2)	C21—C22	1.464 (4)
C7—C8	1.498 (3)	C21—H21A	0.9700
C8—N1	1.436 (2)	C21—H21B	0.9700
C8—C9	1.494 (3)	C22—H22A	0.9700
C8—C10	1.503 (3)	C22—H22B	0.9700
C9—C10	1.470 (3)	N6—C24	1.303 (3)
C9—H9A	0.9700	N6—C23	1.342 (3)
C9—H9B	0.9700	N5—C23	1.305 (2)
C10—H10A	0.9700	N5—N4	1.363 (2)
C10—H10B	0.9700	C12—N1	1.327 (2)
N2—C11	1.309 (3)	C12—H12A	0.9300
N2—N1	1.361 (2)	C11—H11A	0.9300
N3—C12	1.307 (2)	N4—C24	1.330 (2)
N3—C11	1.348 (3)	C24—H24A	0.9300
C13—C18	1.364 (3)	C23—H23A	0.9300

F1—C1—C6	117.4 (2)	C17—C16—C15	116.4 (2)
F1—C1—C2	118.9 (2)	C17—C16—C19	124.0 (2)
C6—C1—C2	123.7 (2)	C15—C16—C19	119.55 (19)
C1—C2—C3	117.9 (2)	F4—C17—C18	118.42 (19)
C1—C2—H2A	121.1	F4—C17—C16	117.9 (2)
C3—C2—H2A	121.1	C18—C17—C16	123.6 (2)
C2—C3—C4	121.47 (19)	C13—C18—C17	116.4 (2)
C2—C3—H3A	119.3	C13—C18—H18A	121.8
C4—C3—H3A	119.3	C17—C18—H18A	121.8
C5—C4—C3	116.77 (19)	O2—C19—C16	119.7 (2)
C5—C4—C7	124.50 (17)	O2—C19—C20	119.5 (2)
C3—C4—C7	118.72 (17)	C16—C19—C20	120.83 (17)
F2—C5—C6	117.88 (17)	N4—C20—C19	116.14 (18)
F2—C5—C4	118.42 (18)	N4—C20—C22	116.23 (18)
C6—C5—C4	123.66 (18)	C19—C20—C22	117.79 (19)
C5—C6—C1	116.47 (19)	N4—C20—C21	117.26 (19)
C5—C6—H6A	121.8	C19—C20—C21	118.64 (19)
C1—C6—H6A	121.8	C22—C20—C21	58.42 (17)
O1—C7—C4	120.29 (19)	C22—C21—C20	60.67 (17)
O1—C7—C8	119.54 (19)	C22—C21—H21A	117.7
C4—C7—C8	120.14 (16)	C20—C21—H21A	117.7
N1—C8—C9	116.98 (16)	C22—C21—H21B	117.7
N1—C8—C7	115.56 (15)	C20—C21—H21B	117.7
C9—C8—C7	118.05 (17)	H21A—C21—H21B	114.8
N1—C8—C10	117.75 (16)	C21—C22—C20	60.91 (16)
C9—C8—C10	58.74 (14)	C21—C22—H22A	117.7
C7—C8—C10	117.95 (17)	C20—C22—H22A	117.7
C10—C9—C8	60.96 (14)	C21—C22—H22B	117.7
C10—C9—H9A	117.7	C20—C22—H22B	117.7
C8—C9—H9A	117.7	H22A—C22—H22B	114.8
C10—C9—H9B	117.7	C24—N6—C23	102.17 (16)
C8—C9—H9B	117.7	C23—N5—N4	102.04 (15)
H9A—C9—H9B	114.8	N3—C12—N1	111.64 (17)
C9—C10—C8	60.30 (14)	N3—C12—H12A	124.2
C9—C10—H10A	117.7	N1—C12—H12A	124.2
C8—C10—H10A	117.7	N2—C11—N3	115.84 (18)
C9—C10—H10B	117.7	N2—C11—H11A	122.1
C8—C10—H10B	117.7	N3—C11—H11A	122.1
H10A—C10—H10B	114.9	C12—N1—N2	108.90 (15)
C11—N2—N1	101.85 (15)	C12—N1—C8	132.04 (15)
C12—N3—C11	101.76 (17)	N2—N1—C8	119.02 (14)
F3—C13—C18	118.3 (2)	C24—N4—N5	108.55 (15)
F3—C13—C14	118.2 (3)	C24—N4—C20	131.78 (17)
C18—C13—C14	123.4 (3)	N5—N4—C20	119.64 (15)
C15—C14—C13	118.1 (2)	N6—C24—N4	111.46 (18)
C15—C14—H14A	120.9	N6—C24—H24A	124.3
C13—C14—H14A	120.9	N4—C24—H24A	124.3
C14—C15—C16	122.0 (2)	N5—C23—N6	115.78 (18)
C14—C15—H15A	119.0	N5—C23—H23A	122.1
C16—C15—H15A	119.0	N6—C23—H23A	122.1

F1—C1—C2—C3	−178.8 (2)	C17—C16—C19—O2	132.8 (2)
C6—C1—C2—C3	1.6 (4)	C15—C16—C19—O2	−45.8 (3)
C1—C2—C3—C4	0.9 (3)	C17—C16—C19—C20	−49.5 (3)
C2—C3—C4—C5	−2.6 (3)	C15—C16—C19—C20	131.9 (2)
C2—C3—C4—C7	178.48 (19)	O2—C19—C20—N4	156.3 (2)
C3—C4—C5—F2	−175.89 (17)	C16—C19—C20—N4	−21.4 (3)
C7—C4—C5—F2	2.9 (3)	O2—C19—C20—C22	11.7 (3)
C3—C4—C5—C6	2.1 (3)	C16—C19—C20—C22	−166.0 (2)
C7—C4—C5—C6	−179.09 (19)	O2—C19—C20—C21	−55.6 (3)
F2—C5—C6—C1	178.18 (18)	C16—C19—C20—C21	126.7 (2)
C4—C5—C6—C1	0.2 (3)	N4—C20—C21—C22	−105.5 (2)
F1—C1—C6—C5	178.23 (19)	C19—C20—C21—C22	106.7 (2)
C2—C1—C6—C5	−2.1 (3)	N4—C20—C22—C21	107.2 (2)
C5—C4—C7—O1	−137.7 (2)	C19—C20—C22—C21	−108.2 (2)
C3—C4—C7—O1	41.0 (3)	C11—N3—C12—N1	−0.4 (2)
C5—C4—C7—C8	44.3 (3)	N1—N2—C11—N3	−0.8 (3)
C3—C4—C7—C8	−136.94 (19)	C12—N3—C11—N2	0.8 (3)
O1—C7—C8—N1	−152.1 (2)	N3—C12—N1—N2	−0.1 (2)
C4—C7—C8—N1	25.9 (2)	N3—C12—N1—C8	−177.66 (18)
O1—C7—C8—C9	−6.6 (3)	C11—N2—N1—C12	0.5 (2)
C4—C7—C8—C9	171.43 (17)	C11—N2—N1—C8	178.46 (17)
O1—C7—C8—C10	60.9 (3)	C9—C8—N1—C12	93.1 (2)
C4—C7—C8—C10	−121.1 (2)	C7—C8—N1—C12	−121.0 (2)
N1—C8—C9—C10	−107.59 (19)	C10—C8—N1—C12	26.0 (3)
C7—C8—C9—C10	107.3 (2)	C9—C8—N1—N2	−84.3 (2)
N1—C8—C10—C9	106.28 (19)	C7—C8—N1—N2	61.6 (2)
C7—C8—C10—C9	−107.5 (2)	C10—C8—N1—N2	−151.36 (17)
F3—C13—C14—C15	178.6 (2)	C23—N5—N4—C24	−0.2 (2)
C18—C13—C14—C15	−0.7 (4)	C23—N5—N4—C20	−178.35 (17)
C13—C14—C15—C16	−1.0 (3)	C19—C20—N4—C24	115.3 (2)
C14—C15—C16—C17	1.9 (3)	C22—C20—N4—C24	−99.5 (3)
C14—C15—C16—C19	−179.5 (2)	C21—C20—N4—C24	−33.2 (3)
C15—C16—C17—F4	176.35 (18)	C19—C20—N4—N5	−67.0 (2)
C19—C16—C17—F4	−2.2 (3)	C22—C20—N4—N5	78.1 (2)
C15—C16—C17—C18	−1.1 (3)	C21—C20—N4—N5	144.4 (2)
C19—C16—C17—C18	−179.7 (2)	C23—N6—C24—N4	0.2 (2)
F3—C13—C18—C17	−177.9 (2)	N5—N4—C24—N6	0.0 (2)
C14—C13—C18—C17	1.4 (3)	C20—N4—C24—N6	177.81 (19)
F4—C17—C18—C13	−177.89 (19)	N4—N5—C23—N6	0.4 (2)
C16—C17—C18—C13	−0.5 (3)	C24—N6—C23—N5	−0.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O2ⁱ	0.93	2.35	3.268 (2)	171
C24—H24A···O1ⁱⁱ	0.93	2.37	3.265 (3)	161

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

Experimental details

Crystal data
Chemical formula	C₁₂H₉F₂N₃O
M_r	249.22
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	9.6067 (11), 11.4840 (13), 11.9127 (14)
α, β, γ (°)	73.652 (1), 84.202 (2), 69.260 (1)
V (Å³)	1179.4 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.49 × 0.40 × 0.38

Data collection
Diffractometer	Rigaku R-AXIS CCD detector diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.983, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	5900, 4080, 2816
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.111, 1.02
No. of reflections	4080
No. of parameters	326
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.16

Computer programs: R-AXIS II Software (Rigaku, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), TEXSAN (Molecular Structure Corporation, 1992).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O2ⁱ	0.93	2.35	3.268 (2)	171.4
C24—H24A···O1ⁱⁱ	0.93	2.37	3.265 (3)	161.3

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

References

Che, X.-Y. & Zhang, W.-N. (2009). Eur. J. Med. Chem. 44, 4218–4226. Web of Science CrossRef PubMed CAS Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Lieven, M. & Leo, J. J. (2005). J. Med. Chem. 48, 2184–2193. PubMed Google Scholar
Molecular Structure Corporation (1992). TEXSAN. MSC, The Woodlands, Texas, USA. Google Scholar
Rigaku (1997). R-AXIS II Software. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tarun, K. M., Debasis, D. & Chittaranjan, S. (1998). Inorg. Chem. 37, 1672–1678. Google Scholar

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Volume 67| Part 11| November 2011| Page o2913

doi:10.1107/S1600536811040037

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