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In the crystal structure of the title compound, C10H9F2N3O, a derivative of triazolinone, there are intra­molecular C—H...O and C—H...N and inter­molecular C—H...F and C—H...O inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806019003/jh2013sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806019003/jh2013Isup2.hkl
Contains datablock I

CCDC reference: 613743

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.043
  • wR factor = 0.121
  • Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C10 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C7
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); 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 (Siemens, 1996); software used to prepare material for publication: SHELXS97.

4-Difluoromethyl-3-methyl-1-phenyl-1H-1,2,4-triazol-5(4H)-one top
Crystal data top
C10H9F2N3OZ = 2
Mr = 225.20F(000) = 232
Triclinic, P1Dx = 1.445 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.2910 (15) ÅCell parameters from 25 reflections
b = 8.2100 (16) Åθ = 11–14°
c = 8.8710 (18) ŵ = 0.12 mm1
α = 85.88 (3)°T = 293 K
β = 80.43 (3)°Block, colourless
γ = 81.71 (3)°0.30 × 0.20 × 0.10 mm
V = 517.53 (19) Å3
Data collection top
Enraf–Nonius CAD-4
diffractometer
1422 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.013
Graphite monochromatorθmax = 26.0°, θmin = 2.3°
ω/2θ scansh = 08
Absorption correction: ψ scan
(North et al., 1968)
k = 1010
Tmin = 0.964, Tmax = 0.988l = 1010
2188 measured reflections3 standard reflections every 200 reflections
2019 independent reflections intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.121 w = 1/[σ2(Fo2) + (0.06P)2 + 0.06P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
2019 reflectionsΔρmax = 0.17 e Å3
146 parametersΔρmin = 0.14 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.131 (13)
Special details top

Experimental. 1H NMR (CDCl3): δ 8.05–8.08 (m, 2H), 7.59–7.64 (m, 2H), 7.41–7.45 (m, 2H), 2.69 (s, 3H).

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
F10.3603 (2)0.70240 (19)1.03226 (14)0.0951 (5)
F20.0949 (2)0.62729 (16)1.01687 (15)0.0940 (5)
O0.1464 (2)1.06459 (16)0.81753 (15)0.0699 (4)
N10.2319 (2)0.77975 (17)0.81876 (16)0.0526 (4)
N20.2493 (2)0.91199 (17)0.59845 (16)0.0506 (4)
N30.3106 (2)0.74604 (19)0.57154 (18)0.0578 (4)
C10.3126 (3)1.0936 (3)0.2050 (3)0.0800 (7)
H1A0.35911.05950.10660.096*
C20.3159 (3)0.9807 (3)0.3270 (2)0.0671 (6)
H2A0.36520.87130.31100.081*
C30.2462 (2)1.0300 (2)0.4730 (2)0.0517 (5)
C40.1735 (3)1.1920 (2)0.4960 (2)0.0680 (6)
H4A0.12551.22640.59410.082*
C50.1727 (3)1.3033 (3)0.3713 (3)0.0802 (7)
H5A0.12401.41300.38640.096*
C60.2422 (3)1.2550 (3)0.2261 (3)0.0756 (6)
H6A0.24151.33090.14310.091*
C70.3502 (4)0.4907 (2)0.7326 (3)0.0800 (7)
H7A0.39320.43980.63660.120*
H7B0.24220.44420.78490.120*
H7C0.44820.47160.79440.120*
C80.2993 (3)0.6709 (2)0.7044 (2)0.0549 (5)
C90.2008 (2)0.9374 (2)0.7510 (2)0.0523 (5)
C100.1977 (3)0.7519 (2)0.9793 (2)0.0632 (5)
H10A0.13310.85231.02820.076*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0925 (10)0.1221 (12)0.0682 (8)0.0056 (8)0.0272 (7)0.0051 (7)
F20.1118 (12)0.0779 (9)0.0878 (9)0.0315 (8)0.0053 (8)0.0140 (7)
O0.0900 (11)0.0501 (8)0.0625 (9)0.0006 (7)0.0038 (7)0.0094 (6)
N10.0555 (9)0.0481 (9)0.0522 (9)0.0022 (7)0.0063 (7)0.0029 (7)
N20.0526 (9)0.0469 (8)0.0507 (9)0.0013 (6)0.0073 (6)0.0049 (6)
N30.0605 (10)0.0517 (9)0.0602 (10)0.0004 (7)0.0111 (7)0.0094 (7)
C10.0957 (18)0.0901 (18)0.0553 (13)0.0245 (14)0.0067 (11)0.0007 (11)
C20.0787 (14)0.0656 (13)0.0572 (12)0.0134 (11)0.0068 (10)0.0051 (10)
C30.0432 (10)0.0562 (11)0.0571 (11)0.0099 (8)0.0110 (8)0.0011 (8)
C40.0730 (14)0.0601 (12)0.0661 (13)0.0002 (10)0.0062 (10)0.0003 (10)
C50.0801 (16)0.0640 (14)0.0911 (18)0.0003 (11)0.0131 (13)0.0127 (12)
C60.0775 (15)0.0800 (16)0.0705 (14)0.0191 (12)0.0188 (11)0.0220 (12)
C70.1015 (18)0.0522 (12)0.0810 (15)0.0067 (11)0.0136 (13)0.0046 (10)
C80.0524 (11)0.0513 (10)0.0603 (12)0.0009 (8)0.0102 (8)0.0065 (9)
C90.0491 (10)0.0510 (10)0.0554 (11)0.0055 (8)0.0044 (8)0.0034 (8)
C100.0690 (13)0.0572 (12)0.0589 (12)0.0040 (10)0.0039 (10)0.0034 (9)
Geometric parameters (Å, º) top
F1—C101.346 (2)C2—C31.377 (3)
F2—C101.345 (2)C2—H2A0.9300
O—C91.219 (2)C3—C41.376 (3)
N1—C81.381 (2)C4—C51.383 (3)
N1—C91.392 (2)C4—H4A0.9300
N1—C101.412 (2)C5—C61.368 (3)
N2—C91.364 (2)C5—H5A0.9300
N2—N31.396 (2)C6—H6A0.9300
N2—C31.423 (2)C7—C81.486 (3)
N3—C81.286 (2)C7—H7A0.9600
C1—C61.364 (3)C7—H7B0.9600
C1—C21.374 (3)C7—H7C0.9600
C1—H1A0.9300C10—H10A0.9800
C8—N1—C9108.30 (15)C1—C6—C5118.9 (2)
C8—N1—C10130.39 (16)C1—C6—H6A120.6
C9—N1—C10121.29 (15)C5—C6—H6A120.6
C9—N2—N3111.71 (14)C8—C7—H7A109.5
C9—N2—C3128.48 (15)C8—C7—H7B109.5
N3—N2—C3119.80 (14)H7A—C7—H7B109.5
C8—N3—N2105.67 (14)C8—C7—H7C109.5
C6—C1—C2121.0 (2)H7A—C7—H7C109.5
C6—C1—H1A119.5H7B—C7—H7C109.5
C2—C1—H1A119.5N3—C8—N1111.07 (16)
C1—C2—C3119.9 (2)N3—C8—C7124.93 (18)
C1—C2—H2A120.1N1—C8—C7124.00 (18)
C3—C2—H2A120.1O—C9—N2130.43 (17)
C4—C3—C2119.81 (18)O—C9—N1126.32 (17)
C4—C3—N2120.75 (17)N2—C9—N1103.24 (15)
C2—C3—N2119.43 (17)F2—C10—F1105.52 (16)
C3—C4—C5119.1 (2)F2—C10—N1110.18 (17)
C3—C4—H4A120.4F1—C10—N1110.13 (16)
C5—C4—H4A120.4F2—C10—H10A110.3
C6—C5—C4121.3 (2)F1—C10—H10A110.3
C6—C5—H5A119.4N1—C10—H10A110.3
C4—C5—H5A119.4
C9—N2—N3—C80.3 (2)C9—N1—C8—N30.9 (2)
C3—N2—N3—C8179.51 (15)C10—N1—C8—N3179.83 (17)
C6—C1—C2—C30.5 (3)C9—N1—C8—C7179.55 (19)
C1—C2—C3—C40.0 (3)C10—N1—C8—C70.6 (3)
C1—C2—C3—N2179.67 (18)N3—N2—C9—O177.90 (18)
C9—N2—C3—C45.7 (3)C3—N2—C9—O1.2 (3)
N3—N2—C3—C4175.19 (16)N3—N2—C9—N10.80 (18)
C9—N2—C3—C2174.60 (17)C3—N2—C9—N1179.93 (15)
N3—N2—C3—C24.5 (2)C8—N1—C9—O177.78 (18)
C2—C3—C4—C50.3 (3)C10—N1—C9—O1.3 (3)
N2—C3—C4—C5179.98 (18)C8—N1—C9—N20.99 (18)
C3—C4—C5—C60.2 (3)C10—N1—C9—N2179.96 (15)
C2—C1—C6—C50.6 (4)C8—N1—C10—F250.0 (3)
C4—C5—C6—C10.3 (4)C9—N1—C10—F2131.18 (18)
N2—N3—C8—N10.4 (2)C8—N1—C10—F166.0 (3)
N2—N3—C8—C7179.93 (18)C9—N1—C10—F1112.82 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2A···N30.932.462.795 (3)102
C4—H4A···O0.932.322.952 (2)125
C7—H7C···F1i0.962.493.368 (3)153
C10—H10A···O0.982.462.857 (2)104
C10—H10A···Oii0.982.303.100 (2)138
Symmetry codes: (i) x+1, y+1, z+2; (ii) x, y+2, z+2.
 

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