1-(2,4-Difluoro­phen­yl)-2-(1H-1,2,4-triazol-1-yl)­ethanone

In the mol­ecule of the title compound, C₁₀H₇F₂N₃O, the dihedral angle between the planar rings is 84.00 (4)°. Inter­molecular C—H...N hydrogen bonds link the mol­ecules and may be effective in stabilizing the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.046
• wR factor = 0.130
• Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)        3000 Deg.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C10 H7 F2 N3 O

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

1-(2,4-Difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone

Crystal data

C10H7F2N3O	Z = 2
Mr = 223.19	F(000) = 228
Triclinic, P1	Dx = 1.511 Mg m^−3
Hall symbol: -P 1	Melting point: 378K-379 K
a = 4.7000 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.853 (2) Å	Cell parameters from 25 reflections
c = 10.898 (2) Å	θ = 10–13°
α = 79.04 (3)°	µ = 0.13 mm^−1
β = 81.81 (3)°	T = 294 K
γ = 88.15 (3)°	Block, white
V = 490.41 (17) Å^3	0.30 × 0.20 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	1449 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.019
Graphite monochromator	θmax = 26.0°, θmin = 1.9°
ω/2θ scans	h = 0→5
Absorption correction: ψ scan (North et al., 1968)	k = −12→12
Tmin = 0.906, Tmax = 0.971	l = −13→13
2168 measured reflections	3 standard reflections every 120 min
1917 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.046	H-atom parameters constrained
wR(F^2) = 0.130	w = 1/[σ^2(Fo^2) + (0.06P)^2 + 0.1P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
1917 reflections	Δρmax = 0.19 e Å^−3
146 parameters	Δρmin = −0.15 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.32 (2)

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	0.2124 (4)	0.04965 (15)	0.07564 (18)	0.1013 (6)
F2	0.1414 (3)	0.34691 (13)	0.36210 (12)	0.0724 (4)
O	−0.4627 (3)	0.58525 (16)	0.17597 (15)	0.0686 (5)
N1	−0.4214 (5)	0.9261 (2)	0.3557 (2)	0.0808 (7)
N2	−0.5595 (4)	0.70858 (18)	0.44170 (18)	0.0634 (5)
N3	−0.3169 (3)	0.70838 (16)	0.35852 (15)	0.0506 (4)
C1	−0.6082 (5)	0.8415 (2)	0.4357 (2)	0.0709 (7)
H1B	−0.7638	0.8747	0.4845	0.085*
C2	−0.2384 (6)	0.8369 (2)	0.3099 (2)	0.0743 (7)
H2B	−0.0760	0.8617	0.2512	0.089*
C3	−0.1757 (4)	0.58046 (19)	0.33795 (19)	0.0512 (5)
H3A	−0.2123	0.5117	0.4148	0.061*
H3B	0.0301	0.5954	0.3193	0.061*
C4	−0.2761 (4)	0.52598 (19)	0.23149 (18)	0.0469 (5)
C5	−0.1395 (4)	0.39803 (18)	0.19461 (18)	0.0465 (5)
C6	0.0570 (4)	0.31441 (19)	0.25827 (19)	0.0516 (5)
C7	0.1769 (5)	0.1968 (2)	0.2205 (2)	0.0634 (6)
H7A	0.3081	0.1427	0.2650	0.076*
C8	0.0942 (5)	0.1636 (2)	0.1150 (2)	0.0669 (6)
C9	−0.0991 (5)	0.2401 (2)	0.0471 (2)	0.0693 (6)
H9A	−0.1506	0.2144	−0.0245	0.083*
C10	−0.2147 (5)	0.3566 (2)	0.0884 (2)	0.0585 (5)
H10A	−0.3475	0.4092	0.0438	0.070*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.1032 (12)	0.0684 (9)	0.1414 (14)	0.0173 (8)	0.0013 (10)	−0.0589 (9)
F2	0.0763 (9)	0.0725 (8)	0.0777 (9)	0.0293 (7)	−0.0330 (7)	−0.0254 (7)
O	0.0726 (10)	0.0663 (9)	0.0785 (10)	0.0258 (8)	−0.0365 (8)	−0.0275 (8)
N1	0.1025 (16)	0.0476 (11)	0.0928 (15)	0.0117 (11)	−0.0050 (13)	−0.0226 (10)
N2	0.0597 (11)	0.0528 (10)	0.0789 (12)	0.0101 (8)	−0.0056 (9)	−0.0204 (9)
N3	0.0519 (9)	0.0443 (9)	0.0607 (10)	0.0088 (7)	−0.0151 (8)	−0.0186 (7)
C1	0.0717 (15)	0.0585 (13)	0.0868 (17)	0.0170 (12)	−0.0093 (13)	−0.0287 (12)
C2	0.0869 (17)	0.0499 (13)	0.0828 (16)	−0.0018 (11)	0.0043 (13)	−0.0162 (11)
C3	0.0483 (10)	0.0477 (11)	0.0627 (12)	0.0111 (8)	−0.0158 (9)	−0.0188 (9)
C4	0.0441 (10)	0.0444 (10)	0.0531 (11)	0.0040 (8)	−0.0085 (8)	−0.0107 (8)
C5	0.0439 (10)	0.0424 (10)	0.0535 (11)	0.0000 (8)	−0.0031 (8)	−0.0121 (8)
C6	0.0487 (11)	0.0467 (11)	0.0597 (12)	0.0053 (8)	−0.0058 (9)	−0.0126 (9)
C7	0.0568 (13)	0.0463 (11)	0.0849 (16)	0.0101 (9)	−0.0037 (11)	−0.0128 (10)
C8	0.0636 (13)	0.0479 (12)	0.0899 (17)	0.0005 (10)	0.0090 (12)	−0.0291 (11)
C9	0.0770 (15)	0.0642 (14)	0.0730 (15)	−0.0041 (12)	−0.0021 (12)	−0.0340 (12)
C10	0.0617 (13)	0.0563 (12)	0.0607 (12)	0.0015 (10)	−0.0104 (10)	−0.0178 (10)

Geometric parameters (Å, º)

F1—C8	1.352 (2)	C3—H3A	0.9700
F2—C6	1.347 (2)	C3—H3B	0.9700
O—C4	1.209 (2)	C4—C5	1.493 (2)
N1—C2	1.326 (3)	C5—C6	1.389 (3)
N1—C1	1.334 (3)	C5—C10	1.392 (3)
N2—C1	1.313 (3)	C6—C7	1.379 (3)
N2—N3	1.352 (2)	C7—C8	1.364 (3)
N3—C2	1.319 (3)	C7—H7A	0.9300
N3—C3	1.446 (2)	C8—C9	1.370 (4)
C1—H1B	0.9300	C9—C10	1.379 (3)
C2—H2B	0.9300	C9—H9A	0.9300
C3—C4	1.505 (3)	C10—H10A	0.9300
C2—N1—C1	101.51 (19)	C5—C4—C3	118.96 (15)
C1—N2—N3	101.81 (18)	C6—C5—C10	116.27 (17)
C2—N3—N2	109.43 (17)	C6—C5—C4	125.53 (17)
C2—N3—C3	129.36 (18)	C10—C5—C4	118.19 (17)
N2—N3—C3	121.15 (16)	F2—C6—C7	116.49 (18)
N2—C1—N1	116.1 (2)	F2—C6—C5	120.15 (16)
N2—C1—H1B	121.9	C7—C6—C5	123.4 (2)
N1—C1—H1B	121.9	C8—C7—C6	116.9 (2)
N3—C2—N1	111.1 (2)	C8—C7—H7A	121.6
N3—C2—H2B	124.4	C6—C7—H7A	121.5
N1—C2—H2B	124.4	F1—C8—C7	117.7 (2)
N3—C3—C4	112.64 (15)	F1—C8—C9	118.9 (2)
N3—C3—H3A	109.1	C7—C8—C9	123.42 (19)
C4—C3—H3A	109.1	C8—C9—C10	117.8 (2)
N3—C3—H3B	109.1	C8—C9—H9A	121.1
C4—C3—H3B	109.1	C10—C9—H9A	121.1
H3A—C3—H3B	107.8	C9—C10—C5	122.2 (2)
O—C4—C5	120.39 (18)	C9—C10—H10A	118.9
O—C4—C3	120.64 (17)	C5—C10—H10A	118.9
C1—N2—N3—C2	0.1 (2)	C3—C4—C5—C10	−173.88 (17)
C1—N2—N3—C3	177.44 (18)	C10—C5—C6—F2	−179.95 (17)
N3—N2—C1—N1	0.7 (3)	C4—C5—C6—F2	−0.6 (3)
C2—N1—C1—N2	−1.2 (3)	C10—C5—C6—C7	0.5 (3)
N2—N3—C2—N1	−0.8 (3)	C4—C5—C6—C7	179.86 (18)
C3—N3—C2—N1	−177.89 (19)	F2—C6—C7—C8	−179.56 (18)
C1—N1—C2—N3	1.1 (3)	C5—C6—C7—C8	0.0 (3)
C2—N3—C3—C4	−91.2 (3)	C6—C7—C8—F1	179.17 (18)
N2—N3—C3—C4	92.0 (2)	C6—C7—C8—C9	−0.3 (3)
N3—C3—C4—O	−2.4 (3)	F1—C8—C9—C10	−179.42 (19)
N3—C3—C4—C5	177.03 (16)	C7—C8—C9—C10	0.0 (4)
O—C4—C5—C6	−173.76 (19)	C8—C9—C10—C5	0.5 (3)
C3—C4—C5—C6	6.8 (3)	C6—C5—C10—C9	−0.8 (3)
O—C4—C5—C10	5.6 (3)	C4—C5—C10—C9	179.82 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···N2	0.97	2.59	3.4933 (5)	156
C7—H7A···N1^i	0.93	2.56	3.438 (3)	159

Symmetry code: (i) x+1, y−1, z.