1-(2,4-Difluoro­phen­yl)-3-(1H-1,2,4-triazol-1-yl)propan-1-one

In the crystal structure of the title compound, C₁₁H₉F₂N₃O, dimers are formed via C—H...O hydrogen bonding. These dimers are located around centres of inversion.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.041
• wR factor = 0.126
• Data-to-parameter ratio = 12.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

1-(2,4-Difluorophenyl)-3-(1H-1,2,4-triazol-1-yl)propan-1-one

Crystal data

C11H9F2N3O	Z = 2
Mr = 237.21	F(000) = 244
Triclinic, P1	Dx = 1.459 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.939 (3) Å	Cell parameters from 1078 reflections
b = 7.743 (4) Å	θ = 2.9–25.1°
c = 10.939 (5) Å	µ = 0.12 mm^−1
α = 100.685 (7)°	T = 294 K
β = 90.650 (8)°	Block, colourless
γ = 110.307 (7)°	0.22 × 0.20 × 0.18 mm
V = 539.8 (4) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	1897 independent reflections
Radiation source: fine-focus sealed tube	1316 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −8→7
Tmin = 0.974, Tmax = 0.979	k = −8→9
2748 measured reflections	l = −11→12

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.126	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0651P)^2 + 0.0629P] where P = (Fo^2 + 2Fc^2)/3
1897 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.15 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
F1	1.0979 (2)	0.8283 (2)	0.25874 (12)	0.0836 (5)
F2	0.69642 (18)	0.7072 (2)	0.59045 (12)	0.0820 (5)
O1	1.1737 (2)	0.6540 (2)	0.78827 (14)	0.0634 (5)
N1	0.7466 (2)	0.7335 (2)	1.03285 (15)	0.0457 (4)
N2	0.6820 (3)	0.8788 (3)	1.03009 (18)	0.0628 (5)
N3	0.5215 (3)	0.7153 (3)	1.17180 (16)	0.0583 (5)
C1	1.2269 (3)	0.7551 (3)	0.55853 (19)	0.0536 (6)
H1	1.3393	0.7497	0.6027	0.064*
C2	1.2476 (3)	0.7884 (3)	0.4392 (2)	0.0603 (6)
H2	1.3719	0.8064	0.4030	0.072*
C3	1.0804 (4)	0.7941 (3)	0.37577 (19)	0.0561 (6)
C4	0.8948 (3)	0.7666 (3)	0.42434 (19)	0.0577 (6)
H4	0.7824	0.7693	0.3787	0.069*
C5	0.8814 (3)	0.7349 (3)	0.54373 (19)	0.0499 (5)
C6	1.0432 (3)	0.7292 (3)	0.61525 (17)	0.0428 (5)
C7	1.0369 (3)	0.6947 (3)	0.74592 (18)	0.0443 (5)
C8	0.8671 (3)	0.7154 (3)	0.82318 (18)	0.0490 (5)
H8A	0.7381	0.6172	0.7877	0.059*
H8B	0.8541	0.8356	0.8212	0.059*
C9	0.9066 (3)	0.7037 (3)	0.95630 (19)	0.0517 (5)
H9A	0.9124	0.5810	0.9586	0.062*
H9B	1.0391	0.7977	0.9904	0.062*
C10	0.5487 (4)	0.8604 (3)	1.1145 (2)	0.0612 (6)
H10	0.4772	0.9424	1.1337	0.073*
C11	0.6498 (3)	0.6397 (3)	1.11675 (19)	0.0522 (5)
H11	0.6695	0.5340	1.1347	0.063*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0919 (11)	0.1147 (12)	0.0499 (8)	0.0371 (9)	0.0187 (7)	0.0288 (8)
F2	0.0476 (7)	0.1512 (15)	0.0606 (9)	0.0473 (9)	0.0130 (6)	0.0298 (9)
O1	0.0668 (10)	0.0854 (12)	0.0583 (10)	0.0496 (9)	0.0095 (8)	0.0196 (8)
N1	0.0449 (9)	0.0536 (10)	0.0445 (9)	0.0201 (8)	0.0097 (7)	0.0181 (8)
N2	0.0702 (12)	0.0604 (12)	0.0748 (13)	0.0348 (10)	0.0296 (10)	0.0308 (10)
N3	0.0612 (11)	0.0711 (13)	0.0494 (10)	0.0272 (10)	0.0172 (9)	0.0208 (9)
C1	0.0436 (11)	0.0660 (14)	0.0544 (13)	0.0246 (10)	0.0071 (10)	0.0097 (10)
C2	0.0494 (12)	0.0746 (16)	0.0562 (14)	0.0201 (11)	0.0191 (11)	0.0143 (11)
C3	0.0648 (14)	0.0603 (14)	0.0428 (12)	0.0213 (11)	0.0119 (10)	0.0103 (10)
C4	0.0598 (14)	0.0722 (15)	0.0443 (12)	0.0300 (12)	0.0001 (10)	0.0066 (10)
C5	0.0410 (11)	0.0622 (14)	0.0479 (12)	0.0220 (10)	0.0093 (9)	0.0068 (10)
C6	0.0412 (10)	0.0428 (11)	0.0444 (11)	0.0169 (8)	0.0073 (9)	0.0045 (8)
C7	0.0436 (11)	0.0416 (11)	0.0488 (12)	0.0176 (9)	0.0047 (9)	0.0072 (9)
C8	0.0454 (11)	0.0580 (13)	0.0484 (12)	0.0218 (10)	0.0096 (9)	0.0158 (10)
C9	0.0494 (11)	0.0629 (13)	0.0523 (12)	0.0275 (10)	0.0108 (10)	0.0192 (10)
C10	0.0646 (14)	0.0630 (14)	0.0657 (15)	0.0313 (12)	0.0234 (12)	0.0184 (12)
C11	0.0569 (12)	0.0604 (13)	0.0455 (12)	0.0229 (11)	0.0061 (10)	0.0211 (10)

Geometric parameters (Å, º)

F1—C3	1.353 (2)	C3—C4	1.361 (3)
F2—C5	1.349 (2)	C4—C5	1.371 (3)
O1—C7	1.212 (2)	C4—H4	0.9300
N1—C11	1.320 (3)	C5—C6	1.379 (3)
N1—N2	1.352 (2)	C6—C7	1.500 (3)
N1—C9	1.455 (3)	C7—C8	1.493 (3)
N2—C10	1.306 (3)	C8—C9	1.504 (3)
N3—C11	1.319 (3)	C8—H8A	0.9700
N3—C10	1.345 (3)	C8—H8B	0.9700
C1—C2	1.376 (3)	C9—H9A	0.9700
C1—C6	1.391 (3)	C9—H9B	0.9700
C1—H1	0.9300	C10—H10	0.9300
C2—C3	1.363 (3)	C11—H11	0.9300
C2—H2	0.9300
C11—N1—N2	109.16 (17)	C1—C6—C7	118.02 (17)
C11—N1—C9	129.11 (18)	O1—C7—C8	120.79 (18)
N2—N1—C9	121.65 (15)	O1—C7—C6	118.90 (17)
C10—N2—N1	102.32 (16)	C8—C7—C6	120.29 (17)
C11—N3—C10	101.58 (17)	C7—C8—C9	111.67 (17)
C2—C1—C6	122.2 (2)	C7—C8—H8A	109.3
C2—C1—H1	118.9	C9—C8—H8A	109.3
C6—C1—H1	118.9	C7—C8—H8B	109.3
C3—C2—C1	117.95 (19)	C9—C8—H8B	109.3
C3—C2—H2	121.0	H8A—C8—H8B	107.9
C1—C2—H2	121.0	N1—C9—C8	111.59 (16)
F1—C3—C4	117.9 (2)	N1—C9—H9A	109.3
F1—C3—C2	118.94 (19)	C8—C9—H9A	109.3
C4—C3—C2	123.2 (2)	N1—C9—H9B	109.3
C3—C4—C5	116.9 (2)	C8—C9—H9B	109.3
C3—C4—H4	121.6	H9A—C9—H9B	108.0
C5—C4—H4	121.6	N2—C10—N3	115.6 (2)
F2—C5—C4	116.24 (18)	N2—C10—H10	122.2
F2—C5—C6	119.93 (18)	N3—C10—H10	122.2
C4—C5—C6	123.84 (19)	N3—C11—N1	111.30 (19)
C5—C6—C1	115.97 (18)	N3—C11—H11	124.4
C5—C6—C7	126.00 (17)	N1—C11—H11	124.4
C11—N1—N2—C10	0.0 (2)	C5—C6—C7—O1	164.5 (2)
C9—N1—N2—C10	−177.00 (19)	C1—C6—C7—O1	−14.4 (3)
C6—C1—C2—C3	−0.5 (3)	C5—C6—C7—C8	−17.0 (3)
C1—C2—C3—F1	179.41 (19)	C1—C6—C7—C8	164.08 (18)
C1—C2—C3—C4	−0.7 (4)	O1—C7—C8—C9	7.1 (3)
F1—C3—C4—C5	−179.10 (19)	C6—C7—C8—C9	−171.35 (17)
C2—C3—C4—C5	1.0 (3)	C11—N1—C9—C8	135.7 (2)
C3—C4—C5—F2	−179.74 (18)	N2—N1—C9—C8	−47.9 (3)
C3—C4—C5—C6	−0.1 (3)	C7—C8—C9—N1	177.03 (16)
F2—C5—C6—C1	178.62 (18)	N1—N2—C10—N3	0.0 (3)
C4—C5—C6—C1	−1.0 (3)	C11—N3—C10—N2	−0.1 (3)
F2—C5—C6—C7	−0.3 (3)	C10—N3—C11—N1	0.1 (2)
C4—C5—C6—C7	−179.90 (19)	N2—N1—C11—N3	−0.1 (3)
C2—C1—C6—C5	1.3 (3)	C9—N1—C11—N3	176.66 (18)
C2—C1—C6—C7	−179.68 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O1^i	0.93	2.36	3.245 (3)	160 (1)

Symmetry code: (i) −x+2, −y+1, −z+2.