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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806035215/bx2021sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806035215/bx2021Isup2.hkl
Contains datablock I

CCDC reference: 624015

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

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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 top

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 top
Crystal data top
C11H9F2N3OZ = 2
Mr = 237.21F(000) = 244
Triclinic, P1Dx = 1.459 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.939 (3) ÅCell parameters from 1078 reflections
b = 7.743 (4) Åθ = 2.9–25.1°
c = 10.939 (5) ŵ = 0.12 mm1
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) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
1897 independent reflections
Radiation source: fine-focus sealed tube1316 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
φ and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1997)
h = 87
Tmin = 0.974, Tmax = 0.979k = 89
2748 measured reflectionsl = 1112
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0651P)2 + 0.0629P]
where P = (Fo2 + 2Fc2)/3
1897 reflections(Δ/σ)max < 0.001
154 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = 0.21 e Å3
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
xyzUiso*/Ueq
F11.0979 (2)0.8283 (2)0.25874 (12)0.0836 (5)
F20.69642 (18)0.7072 (2)0.59045 (12)0.0820 (5)
O11.1737 (2)0.6540 (2)0.78827 (14)0.0634 (5)
N10.7466 (2)0.7335 (2)1.03285 (15)0.0457 (4)
N20.6820 (3)0.8788 (3)1.03009 (18)0.0628 (5)
N30.5215 (3)0.7153 (3)1.17180 (16)0.0583 (5)
C11.2269 (3)0.7551 (3)0.55853 (19)0.0536 (6)
H11.33930.74970.60270.064*
C21.2476 (3)0.7884 (3)0.4392 (2)0.0603 (6)
H21.37190.80640.40300.072*
C31.0804 (4)0.7941 (3)0.37577 (19)0.0561 (6)
C40.8948 (3)0.7666 (3)0.42434 (19)0.0577 (6)
H40.78240.76930.37870.069*
C50.8814 (3)0.7349 (3)0.54373 (19)0.0499 (5)
C61.0432 (3)0.7292 (3)0.61525 (17)0.0428 (5)
C71.0369 (3)0.6947 (3)0.74592 (18)0.0443 (5)
C80.8671 (3)0.7154 (3)0.82318 (18)0.0490 (5)
H8A0.73810.61720.78770.059*
H8B0.85410.83560.82120.059*
C90.9066 (3)0.7037 (3)0.95630 (19)0.0517 (5)
H9A0.91240.58100.95860.062*
H9B1.03910.79770.99040.062*
C100.5487 (4)0.8604 (3)1.1145 (2)0.0612 (6)
H100.47720.94241.13370.073*
C110.6498 (3)0.6397 (3)1.11675 (19)0.0522 (5)
H110.66950.53401.13470.063*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0919 (11)0.1147 (12)0.0499 (8)0.0371 (9)0.0187 (7)0.0288 (8)
F20.0476 (7)0.1512 (15)0.0606 (9)0.0473 (9)0.0130 (6)0.0298 (9)
O10.0668 (10)0.0854 (12)0.0583 (10)0.0496 (9)0.0095 (8)0.0196 (8)
N10.0449 (9)0.0536 (10)0.0445 (9)0.0201 (8)0.0097 (7)0.0181 (8)
N20.0702 (12)0.0604 (12)0.0748 (13)0.0348 (10)0.0296 (10)0.0308 (10)
N30.0612 (11)0.0711 (13)0.0494 (10)0.0272 (10)0.0172 (9)0.0208 (9)
C10.0436 (11)0.0660 (14)0.0544 (13)0.0246 (10)0.0071 (10)0.0097 (10)
C20.0494 (12)0.0746 (16)0.0562 (14)0.0201 (11)0.0191 (11)0.0143 (11)
C30.0648 (14)0.0603 (14)0.0428 (12)0.0213 (11)0.0119 (10)0.0103 (10)
C40.0598 (14)0.0722 (15)0.0443 (12)0.0300 (12)0.0001 (10)0.0066 (10)
C50.0410 (11)0.0622 (14)0.0479 (12)0.0220 (10)0.0093 (9)0.0068 (10)
C60.0412 (10)0.0428 (11)0.0444 (11)0.0169 (8)0.0073 (9)0.0045 (8)
C70.0436 (11)0.0416 (11)0.0488 (12)0.0176 (9)0.0047 (9)0.0072 (9)
C80.0454 (11)0.0580 (13)0.0484 (12)0.0218 (10)0.0096 (9)0.0158 (10)
C90.0494 (11)0.0629 (13)0.0523 (12)0.0275 (10)0.0108 (10)0.0192 (10)
C100.0646 (14)0.0630 (14)0.0657 (15)0.0313 (12)0.0234 (12)0.0184 (12)
C110.0569 (12)0.0604 (13)0.0455 (12)0.0229 (11)0.0061 (10)0.0211 (10)
Geometric parameters (Å, º) top
F1—C31.353 (2)C3—C41.361 (3)
F2—C51.349 (2)C4—C51.371 (3)
O1—C71.212 (2)C4—H40.9300
N1—C111.320 (3)C5—C61.379 (3)
N1—N21.352 (2)C6—C71.500 (3)
N1—C91.455 (3)C7—C81.493 (3)
N2—C101.306 (3)C8—C91.504 (3)
N3—C111.319 (3)C8—H8A0.9700
N3—C101.345 (3)C8—H8B0.9700
C1—C21.376 (3)C9—H9A0.9700
C1—C61.391 (3)C9—H9B0.9700
C1—H10.9300C10—H100.9300
C2—C31.363 (3)C11—H110.9300
C2—H20.9300
C11—N1—N2109.16 (17)C1—C6—C7118.02 (17)
C11—N1—C9129.11 (18)O1—C7—C8120.79 (18)
N2—N1—C9121.65 (15)O1—C7—C6118.90 (17)
C10—N2—N1102.32 (16)C8—C7—C6120.29 (17)
C11—N3—C10101.58 (17)C7—C8—C9111.67 (17)
C2—C1—C6122.2 (2)C7—C8—H8A109.3
C2—C1—H1118.9C9—C8—H8A109.3
C6—C1—H1118.9C7—C8—H8B109.3
C3—C2—C1117.95 (19)C9—C8—H8B109.3
C3—C2—H2121.0H8A—C8—H8B107.9
C1—C2—H2121.0N1—C9—C8111.59 (16)
F1—C3—C4117.9 (2)N1—C9—H9A109.3
F1—C3—C2118.94 (19)C8—C9—H9A109.3
C4—C3—C2123.2 (2)N1—C9—H9B109.3
C3—C4—C5116.9 (2)C8—C9—H9B109.3
C3—C4—H4121.6H9A—C9—H9B108.0
C5—C4—H4121.6N2—C10—N3115.6 (2)
F2—C5—C4116.24 (18)N2—C10—H10122.2
F2—C5—C6119.93 (18)N3—C10—H10122.2
C4—C5—C6123.84 (19)N3—C11—N1111.30 (19)
C5—C6—C1115.97 (18)N3—C11—H11124.4
C5—C6—C7126.00 (17)N1—C11—H11124.4
C11—N1—N2—C100.0 (2)C5—C6—C7—O1164.5 (2)
C9—N1—N2—C10177.00 (19)C1—C6—C7—O114.4 (3)
C6—C1—C2—C30.5 (3)C5—C6—C7—C817.0 (3)
C1—C2—C3—F1179.41 (19)C1—C6—C7—C8164.08 (18)
C1—C2—C3—C40.7 (4)O1—C7—C8—C97.1 (3)
F1—C3—C4—C5179.10 (19)C6—C7—C8—C9171.35 (17)
C2—C3—C4—C51.0 (3)C11—N1—C9—C8135.7 (2)
C3—C4—C5—F2179.74 (18)N2—N1—C9—C847.9 (3)
C3—C4—C5—C60.1 (3)C7—C8—C9—N1177.03 (16)
F2—C5—C6—C1178.62 (18)N1—N2—C10—N30.0 (3)
C4—C5—C6—C11.0 (3)C11—N3—C10—N20.1 (3)
F2—C5—C6—C70.3 (3)C10—N3—C11—N10.1 (2)
C4—C5—C6—C7179.90 (19)N2—N1—C11—N30.1 (3)
C2—C1—C6—C51.3 (3)C9—N1—C11—N3176.66 (18)
C2—C1—C6—C7179.68 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H11···O1i0.932.363.245 (3)160 (1)
Symmetry code: (i) x+2, y+1, z+2.
 

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