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The molecule of the title compound, C10H9FN4O, is almost planar. In the 1,2,4-triazole moiety, the C=N, C-N and N-N bond lengths are normal. The crystal structure is stabilized by intra- and intermolecular hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803013047/bt6280sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803013047/bt6280Isup2.hkl
Contains datablock I

CCDC reference: 221697

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.037
  • wR factor = 0.107
  • Data-to-parameter ratio = 19.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: WinGX (Farrugia, 1997) and PARST (Nardelli, 1995).

4-(p-Fluorobenzylideneamino)-3-methyl-4,5-dihydro-1H-1,2,4-triazol-5-one top
Crystal data top
C10H9FN4OF(000) = 456
Mr = 220.21Dx = 1.415 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 7.0012 (8) ÅCell parameters from 8026 reflections
b = 13.8430 (12) Åθ = 1.5–29.5°
c = 11.1307 (11) ŵ = 0.11 mm1
β = 106.572 (8)°T = 293 K
V = 1033.95 (18) Å3Prismatic, colourless
Z = 40.4 × 0.37 × 0.3 mm
Data collection top
Stoe IPDS-II
diffractometer
1657 reflections with I > 2σ(I)
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focusRint = 0.000
Plane graphite monochromatorθmax = 29.5°, θmin = 1.5°
Detector resolution: 6.67 pixels mm-1h = 99
rotation method scansk = 1919
10015 measured reflectionsl = 1515
2861 independent reflections
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)] = 0.037H-atom parameters constrained
wR(F2) = 0.107 w = 1/[σ2(Fo2) + (0.0664P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.89(Δ/σ)max < 0.001
2861 reflectionsΔρmax = 0.14 e Å3
147 parametersΔρmin = 0.20 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.054 (11)
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
O10.09601 (15)0.55573 (7)0.16483 (8)0.0643 (3)
N10.17354 (14)0.41525 (7)0.28943 (8)0.0463 (2)
N40.22909 (15)0.44457 (7)0.41330 (8)0.0486 (2)
N30.10686 (17)0.30559 (8)0.13995 (9)0.0577 (3)
C40.21359 (17)0.53276 (9)0.43871 (10)0.0503 (3)
H40.16800.57770.37480.060*
C10.11110 (18)0.46737 (9)0.17835 (10)0.0500 (3)
N20.07382 (18)0.39789 (8)0.09126 (9)0.0596 (3)
H20.03300.40960.01220.071*
C30.2264 (2)0.24182 (10)0.35482 (12)0.0632 (4)
H3A0.18550.18030.31620.095*
H3B0.16310.25270.41960.095*
H3C0.36840.24230.39050.095*
F10.41026 (16)0.65176 (10)0.93557 (8)0.1079 (4)
C50.26844 (17)0.56322 (9)0.57039 (10)0.0499 (3)
C20.16824 (18)0.31863 (9)0.25981 (10)0.0490 (3)
C60.2527 (2)0.65941 (11)0.59875 (13)0.0623 (3)
H60.20880.70410.53440.075*
C100.3333 (2)0.49743 (11)0.66734 (11)0.0609 (3)
H100.34420.43240.64920.073*
C80.3644 (2)0.62288 (14)0.81434 (12)0.0714 (4)
C90.3819 (2)0.52754 (13)0.79032 (12)0.0721 (4)
H90.42580.48360.85550.087*
C70.3020 (2)0.69012 (12)0.72261 (15)0.0726 (4)
H70.29250.75490.74220.087*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0990 (7)0.0497 (5)0.0388 (4)0.0096 (5)0.0111 (4)0.0034 (4)
N10.0574 (5)0.0488 (6)0.0303 (4)0.0004 (4)0.0084 (4)0.0014 (4)
N40.0565 (5)0.0563 (6)0.0309 (4)0.0024 (5)0.0088 (4)0.0006 (4)
N30.0790 (7)0.0508 (6)0.0408 (5)0.0026 (5)0.0130 (5)0.0002 (4)
C40.0586 (7)0.0556 (7)0.0351 (5)0.0004 (5)0.0107 (5)0.0021 (5)
C10.0635 (7)0.0512 (7)0.0332 (5)0.0042 (5)0.0105 (5)0.0026 (5)
N20.0894 (8)0.0524 (6)0.0317 (4)0.0069 (5)0.0087 (4)0.0017 (4)
C30.0807 (9)0.0546 (8)0.0512 (7)0.0011 (6)0.0138 (6)0.0098 (6)
F10.1119 (8)0.1509 (11)0.0536 (5)0.0215 (7)0.0118 (5)0.0464 (6)
C50.0492 (6)0.0611 (7)0.0389 (5)0.0051 (5)0.0118 (4)0.0039 (5)
C20.0580 (7)0.0478 (7)0.0399 (6)0.0009 (5)0.0118 (5)0.0021 (5)
C60.0670 (8)0.0638 (9)0.0566 (7)0.0034 (6)0.0183 (6)0.0069 (6)
C100.0698 (8)0.0688 (9)0.0403 (6)0.0029 (6)0.0095 (5)0.0022 (6)
C80.0650 (8)0.1016 (13)0.0451 (7)0.0171 (8)0.0114 (6)0.0242 (8)
C90.0783 (9)0.0936 (12)0.0385 (6)0.0062 (8)0.0072 (6)0.0033 (7)
C70.0741 (9)0.0754 (10)0.0705 (9)0.0128 (7)0.0241 (7)0.0291 (8)
Geometric parameters (Å, º) top
O1—C11.2332 (15)C3—H3B0.9600
N1—C21.3755 (15)C3—H3C0.9600
N1—N41.3824 (12)F1—C81.3552 (15)
N1—C11.3899 (14)C5—C61.3801 (19)
N4—C41.2648 (16)C5—C101.3859 (19)
N3—C21.2923 (14)C6—C71.3890 (19)
N3—N21.3814 (15)C6—H60.9300
C4—C51.4671 (15)C10—C91.3775 (18)
C4—H40.9300C10—H100.9300
C1—N21.3374 (16)C8—C71.358 (2)
N2—H20.8600C8—C91.359 (2)
C3—C21.4729 (17)C9—H90.9300
C3—H3A0.9600C7—H70.9300
C2—N1—N4120.35 (9)C6—C5—C4119.38 (12)
C2—N1—C1108.15 (9)C10—C5—C4121.55 (12)
N4—N1—C1131.48 (10)N3—C2—N1111.20 (10)
C4—N4—N1119.26 (10)N3—C2—C3125.65 (12)
C2—N3—N2104.18 (10)N1—C2—C3123.15 (10)
N4—C4—C5119.09 (11)C5—C6—C7120.59 (14)
N4—C4—H4120.5C5—C6—H6119.7
C5—C4—H4120.5C7—C6—H6119.7
O1—C1—N2129.24 (10)C9—C10—C5120.53 (14)
O1—C1—N1128.15 (10)C9—C10—H10119.7
N2—C1—N1102.61 (10)C5—C10—H10119.7
C1—N2—N3113.87 (10)F1—C8—C7118.70 (16)
C1—N2—H2123.1F1—C8—C9118.25 (15)
N3—N2—H2123.1C7—C8—C9123.04 (13)
C2—C3—H3A109.5C8—C9—C10118.61 (14)
C2—C3—H3B109.5C8—C9—H9120.7
H3A—C3—H3B109.5C10—C9—H9120.7
C2—C3—H3C109.5C8—C7—C6118.16 (15)
H3A—C3—H3C109.5C8—C7—H7120.9
H3B—C3—H3C109.5C6—C7—H7120.9
C6—C5—C10119.06 (12)
C2—N1—N4—C4172.87 (11)N4—N1—C2—N3177.92 (10)
C1—N1—N4—C44.96 (18)C1—N1—C2—N30.37 (14)
N1—N4—C4—C5178.63 (10)N4—N1—C2—C32.17 (18)
C2—N1—C1—O1179.62 (13)C1—N1—C2—C3179.54 (12)
N4—N1—C1—O12.4 (2)C10—C5—C6—C70.3 (2)
C2—N1—C1—N20.10 (13)C4—C5—C6—C7179.43 (12)
N4—N1—C1—N2178.14 (11)C6—C5—C10—C90.1 (2)
O1—C1—N2—N3179.97 (13)C4—C5—C10—C9179.27 (13)
N1—C1—N2—N30.53 (14)F1—C8—C9—C10179.25 (13)
C2—N3—N2—C10.76 (15)C7—C8—C9—C100.3 (2)
N4—C4—C5—C6179.70 (12)C5—C10—C9—C80.2 (2)
N4—C4—C5—C101.15 (18)F1—C8—C7—C6179.12 (12)
N2—N3—C2—N10.66 (14)C9—C8—C7—C60.5 (2)
N2—N3—C2—C3179.25 (12)C5—C6—C7—C80.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O1i0.861.982.832 (1)172
C3—H3C···F1ii0.962.453.175 (2)132
C4—H4···O10.932.272.939 (2)129
Symmetry codes: (i) x, y+1, z; (ii) x+1, y1/2, z+3/2.
 

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