Download citation
Download citation
link to html
In the crystal structure of the title compound, C16H13N4OF, molecules are linked through intermolecular N—H...O hydrogen bonds to form dimers. The dimers are held together by van der Waals interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803011474/cv6196sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803011474/cv6196Isup2.hkl
Contains datablock I

CCDC reference: 217616

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.047
  • wR factor = 0.153
  • Data-to-parameter ratio = 16.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Amber Alert Alert Level B:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 29.27 From the CIF: _reflns_number_total 3550 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 3953 Completeness (_total/calc) 89.81% Alert B: < 90% complete (theta max?)
Yellow Alert Alert Level C:
PLAT_031 Alert C Refined Extinction Parameter within Range .... 2.80 Sigma
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
1 Alert Level C = Please check

Comment top

Most Schiff bases possess antibacterial, anticancer, anti-inflammatory and antitoxic activities (Williams, 1972), and sulfur-containing Schiff bases are particularly effective. For example, the 4-amino-3-methyl-1,2,4-triazole-5-thione derivative of p-nitrophenylaldehyde is known as a highly effective inhibitor of Staphylococcus aureus (Liu et al., 1999). As part of our continuing study of Schiff bases of amine and 1,2,4-triazole derivatives, we have structurally characterized the title compounds, (I) (Fig. 1) (Kahveci et al., 2000; Çoruh et al., 2003; Işık et al., 2003).

The bonds and angles in (I) (Table 1) are consistent with those in similar substituted triazoles (Kahveci et al., 2000; Çoruh et al., 2003; Işık et al., 2003). Benzyl rings and 1,2,4-triazole ring are almost planar, with a maximum deviation of 0.008 (2) Å for N2. The dihedral angles between the 1,2,4-triazole ring and benzyl rings C1–C6 and C11–C16 are 179.3 (1) and 104.9 (1)°, respectively, and the dihedral angle between the benzyl rings is 104.9 (1)°.

The molecules of (I) form hydrogen-bonded dimers through the N—H···O interactions involving triazole atom O1 and the adjacent protonated N2 atom on the ring, shown as dashed lines in Fig.2. This feature appears to be common in Schiff bases of 4-amino-3-alkyl-1,2,4-triazole-5-thiones (Sen et al., 1998). The molecule has also an intramolecular C7—H7···O1 contact (Table 2).

Experimental top

The corresponding amino compound (1.90 g., 0.01 mol) was heated in an oil both with 4-fluorobenzene (1.04 ml, 0.01 mol) at 428–433 K for one hour and then allowed to cool. The solid product was recrystallized from ethanol (yield; 96%) to give the desired compound (I) (m.p. = 466–467 K). Calculated: C 64.86, H 4.42, N 18.91%; found: C 64.83, H 4.26, N 18.35%. IR data (KBr/cm−1): 3250 (N—H), 1720 (CO), 1620, 1600 (CN), 700, 680, 840 (aromatic). 1H NMR (CDCl3, δ/p.p.m.): 4.18 (CH2,s, 2H), 9,78 (CH, s, 1H), 10.10 (NH, s, 1H); Ar—H: 7.04–7.40 (m, 7H), 7.70 (d, 2H).

Refinement top

H atoms were located geometrically and refined using a riding model, fixing the aromatic C—H distance at 0.93 Å, the C—H2 distance 0.97 Å and the N—H distance at 0.86 Å.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002); 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).

Figures top
[Figure 1] Fig. 1. The structure of (I), showing ellipsoids drawn at the 50% probability level and the atom-numbering scheme.
[Figure 2] Fig. 2. A packing diagram showing the crystal packing in (I). Intermolecular N—H···O hydrogen bonds are shown as dashed lines.
3-Benzyl-4-(p-Fluorobenzylidenamino)-4,5-dihydro-1H-1,2,4-triazol-5-one top
Crystal data top
C16H13FN4OZ = 2
Mr = 296.30F(000) = 308
Triclinic, P1Dx = 1.359 Mg m3
a = 7.0290 (15) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.141 (2) ÅCell parameters from 8077 reflections
c = 11.205 (3) Åθ = 0.0–29.5°
α = 96.40 (2)°µ = 0.10 mm1
β = 102.944 (17)°T = 293 K
γ = 108.394 (16)°Prismatic, colourless
V = 724.2 (3) Å30.75 × 0.46 × 0.22 mm
Data collection top
Stoe IPDS 2
diffractometer
2341 reflections with I > 2σ(I)
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focusRint = 0.000
Plane graphite monochromatorθmax = 29.3°, θmin = 1.9°
Detector resolution: 6.67 pixels mm-1h = 90
rotation method scansk = 1212
3550 measured reflectionsl = 1415
3550 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)] = 0.047Only H-atom coordinates refined
wR(F2) = 0.153 w = 1/[σ2(Fo2) + (0.1093P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
3550 reflectionsΔρmax = 0.17 e Å3
212 parametersΔρmin = 0.17 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.028 (10)
Crystal data top
C16H13FN4Oγ = 108.394 (16)°
Mr = 296.30V = 724.2 (3) Å3
Triclinic, P1Z = 2
a = 7.0290 (15) ÅMo Kα radiation
b = 10.141 (2) ŵ = 0.10 mm1
c = 11.205 (3) ÅT = 293 K
α = 96.40 (2)°0.75 × 0.46 × 0.22 mm
β = 102.944 (17)°
Data collection top
Stoe IPDS 2
diffractometer
2341 reflections with I > 2σ(I)
3550 measured reflectionsRint = 0.000
3550 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.153Only H-atom coordinates refined
S = 1.00Δρmax = 0.17 e Å3
3550 reflectionsΔρmin = 0.17 e Å3
212 parameters
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
F11.4326 (2)0.61860 (15)0.06208 (10)0.1022 (4)
O11.11115 (17)0.55461 (11)0.82528 (10)0.0617 (3)
N11.17520 (16)0.36093 (13)0.64075 (10)0.0500 (3)
N21.0435 (2)0.34595 (13)0.96421 (12)0.0593 (3)
H2N1.02140.37581.03310.088 (6)*
N31.0307 (2)0.20838 (14)0.95922 (12)0.0590 (3)
N41.11808 (16)0.33816 (12)0.77025 (10)0.0479 (3)
C11.3825 (2)0.5857 (2)0.18884 (15)0.0668 (5)
C21.3695 (2)0.68901 (19)0.25405 (17)0.0682 (5)
H21.39640.78080.21340.084 (6)*
C31.3146 (2)0.65300 (17)0.38293 (15)0.0607 (4)
H31.30430.72190.42970.070 (5)*
C41.27424 (19)0.51637 (15)0.44418 (13)0.0514 (3)
C51.2921 (2)0.41500 (18)0.37347 (14)0.0608 (4)
H51.26690.32320.41310.071 (5)*
C61.3469 (3)0.4491 (2)0.24488 (16)0.0708 (5)
H61.35900.38120.19710.091 (7)*
C71.2139 (2)0.48508 (16)0.58112 (14)0.0538 (3)
H71.20390.55650.62480.068 (5)*
C81.0934 (2)0.42931 (15)0.85141 (13)0.0512 (3)
C91.0778 (2)0.20621 (15)0.84086 (13)0.0503 (3)
C101.0716 (2)0.07868 (16)0.78746 (14)0.0547 (3)
H10A1.09140.00990.84640.068 (5)*
H10B1.18480.10420.71160.049 (4)*
C110.8661 (2)0.01279 (14)0.75829 (13)0.0500 (3)
C120.8509 (3)0.02903 (18)0.63691 (14)0.0621 (4)
H120.96840.08140.57180.065 (5)*
C130.6634 (3)0.0318 (2)0.61191 (18)0.0757 (5)
H130.65510.02110.52990.135 (9)*
C140.4882 (3)0.1079 (2)0.7073 (2)0.0794 (5)
H140.36150.14910.69020.094 (6)*
C150.5010 (3)0.1231 (2)0.8279 (2)0.0845 (6)
H150.38230.17370.89290.087 (6)*
C160.6887 (3)0.06387 (18)0.85354 (16)0.0701 (5)
H160.69600.07550.93560.103 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.1184 (9)0.1180 (11)0.0591 (6)0.0442 (8)0.0119 (6)0.0090 (6)
O10.0787 (7)0.0414 (6)0.0650 (6)0.0184 (5)0.0220 (5)0.0134 (4)
N10.0482 (6)0.0469 (7)0.0545 (6)0.0147 (5)0.0173 (4)0.0078 (5)
N20.0783 (8)0.0479 (7)0.0566 (7)0.0227 (6)0.0250 (6)0.0145 (5)
N30.0731 (8)0.0490 (8)0.0599 (7)0.0235 (6)0.0255 (6)0.0100 (5)
N40.0499 (6)0.0421 (6)0.0530 (6)0.0148 (4)0.0186 (4)0.0097 (4)
C10.0609 (8)0.0770 (12)0.0566 (8)0.0259 (8)0.0111 (6)0.0049 (8)
C20.0588 (8)0.0575 (10)0.0782 (11)0.0211 (7)0.0107 (7)0.0114 (8)
C30.0587 (8)0.0482 (9)0.0712 (9)0.0202 (6)0.0121 (6)0.0035 (7)
C40.0440 (6)0.0476 (8)0.0604 (8)0.0153 (5)0.0147 (5)0.0041 (6)
C50.0684 (9)0.0507 (9)0.0624 (9)0.0210 (7)0.0187 (7)0.0054 (7)
C60.0809 (11)0.0687 (12)0.0635 (9)0.0281 (9)0.0187 (8)0.0132 (8)
C70.0537 (7)0.0474 (8)0.0605 (8)0.0174 (6)0.0169 (6)0.0094 (6)
C80.0517 (7)0.0444 (8)0.0591 (8)0.0134 (5)0.0218 (6)0.0131 (6)
C90.0521 (7)0.0449 (8)0.0573 (7)0.0176 (5)0.0217 (6)0.0075 (6)
C100.0609 (8)0.0449 (8)0.0644 (8)0.0257 (6)0.0195 (6)0.0094 (6)
C110.0621 (8)0.0343 (7)0.0575 (7)0.0216 (6)0.0164 (6)0.0108 (5)
C120.0717 (9)0.0582 (10)0.0578 (8)0.0241 (7)0.0152 (7)0.0190 (7)
C130.0914 (12)0.0756 (12)0.0746 (11)0.0325 (10)0.0396 (9)0.0289 (9)
C140.0743 (11)0.0595 (11)0.1118 (15)0.0201 (8)0.0425 (10)0.0221 (10)
C150.0665 (10)0.0678 (12)0.0965 (14)0.0053 (8)0.0154 (9)0.0063 (10)
C160.0745 (10)0.0586 (10)0.0652 (9)0.0142 (8)0.0175 (7)0.0047 (7)
Geometric parameters (Å, º) top
F1—C11.3598 (19)C5—H50.9300
O1—C81.2314 (18)C6—H60.9304
N1—C71.2730 (19)C7—H70.9299
N1—N41.3878 (16)C9—C101.477 (2)
N2—C81.3459 (19)C10—C111.514 (2)
N2—N31.3777 (19)C10—H10A0.9698
N2—H2N0.8596C10—H10B0.9702
N3—C91.2975 (19)C11—C161.380 (2)
N4—C91.3859 (18)C11—C121.384 (2)
N4—C81.3890 (19)C12—C131.374 (2)
C1—C21.357 (3)C12—H120.9294
C1—C61.376 (3)C13—C141.372 (3)
C2—C31.383 (2)C13—H130.9300
C2—H20.9302C14—C151.369 (3)
C3—C41.387 (2)C14—H140.9294
C3—H30.9301C15—C161.375 (3)
C4—C51.385 (2)C15—H150.9297
C4—C71.466 (2)C16—H160.9294
C5—C61.379 (2)
C7—N1—N4117.68 (13)O1—C8—N4128.10 (13)
C8—N2—N3113.84 (13)N2—C8—N4102.63 (12)
C8—N2—H2N123.1N3—C9—N4110.75 (13)
N3—N2—H2N123.1N3—C9—C10125.16 (13)
C9—N3—N2104.55 (12)N4—C9—C10123.88 (13)
C9—N4—N1120.65 (12)C9—C10—C11111.28 (12)
C9—N4—C8108.21 (11)C9—C10—H10A109.3
N1—N4—C8131.14 (12)C11—C10—H10A109.3
C2—C1—F1118.45 (16)C9—C10—H10B109.4
C2—C1—C6123.13 (16)C11—C10—H10B109.4
F1—C1—C6118.41 (18)H10A—C10—H10B108.0
C1—C2—C3117.67 (15)C16—C11—C12118.65 (14)
C1—C2—H2121.2C16—C11—C10120.16 (14)
C3—C2—H2121.2C12—C11—C10121.18 (13)
C2—C3—C4121.53 (16)C13—C12—C11120.49 (16)
C2—C3—H3119.3C13—C12—H12119.7
C4—C3—H3119.2C11—C12—H12119.8
C5—C4—C3118.65 (14)C14—C13—C12120.32 (17)
C5—C4—C7122.70 (13)C14—C13—H13119.9
C3—C4—C7118.65 (15)C12—C13—H13119.8
C6—C5—C4120.59 (15)C15—C14—C13119.63 (17)
C6—C5—H5119.7C15—C14—H14120.2
C4—C5—H5119.7C13—C14—H14120.2
C1—C6—C5118.42 (18)C14—C15—C16120.39 (17)
C1—C6—H6120.8C14—C15—H15119.9
C5—C6—H6120.8C16—C15—H15119.7
N1—C7—C4120.54 (15)C15—C16—C11120.51 (17)
N1—C7—H7119.7C15—C16—H16119.7
C4—C7—H7119.7C11—C16—H16119.8
O1—C8—N2129.27 (14)
C8—N2—N3—C91.31 (16)C9—N4—C8—N20.94 (14)
C7—N1—N4—C9178.74 (12)N1—N4—C8—N2178.05 (12)
C7—N1—N4—C80.14 (19)N2—N3—C9—N40.62 (15)
F1—C1—C2—C3178.80 (13)N2—N3—C9—C10175.56 (13)
C6—C1—C2—C31.0 (3)N1—N4—C9—N3178.91 (10)
C1—C2—C3—C40.1 (2)C8—N4—C9—N30.20 (15)
C2—C3—C4—C50.7 (2)N1—N4—C9—C106.07 (19)
C2—C3—C4—C7179.16 (13)C8—N4—C9—C10174.82 (12)
C3—C4—C5—C60.6 (2)N3—C9—C10—C1194.75 (16)
C7—C4—C5—C6179.21 (14)N4—C9—C10—C1179.54 (16)
C2—C1—C6—C51.1 (3)C9—C10—C11—C1675.33 (18)
F1—C1—C6—C5178.73 (14)C9—C10—C11—C12103.94 (17)
C4—C5—C6—C10.2 (2)C16—C11—C12—C130.9 (3)
N4—N1—C7—C4179.74 (10)C10—C11—C12—C13179.82 (16)
C5—C4—C7—N10.0 (2)C11—C12—C13—C140.8 (3)
C3—C4—C7—N1179.86 (12)C12—C13—C14—C150.0 (3)
N3—N2—C8—O1177.93 (13)C13—C14—C15—C160.7 (3)
N3—N2—C8—N41.39 (15)C14—C15—C16—C110.6 (3)
C9—N4—C8—O1178.40 (13)C12—C11—C16—C150.2 (3)
N1—N4—C8—O12.6 (2)C10—C11—C16—C15179.48 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2N···O1i0.861.972.799 (2)161
C7—H7···O10.932.192.893 (2)132
Symmetry code: (i) x2, y1, z+2.

Experimental details

Crystal data
Chemical formulaC16H13FN4O
Mr296.30
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)7.0290 (15), 10.141 (2), 11.205 (3)
α, β, γ (°)96.40 (2), 102.944 (17), 108.394 (16)
V3)724.2 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.75 × 0.46 × 0.22
Data collection
DiffractometerStoe IPDS 2
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
3550, 3550, 2341
Rint0.000
(sin θ/λ)max1)0.688
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.153, 1.00
No. of reflections3550
No. of parameters212
H-atom treatmentOnly H-atom coordinates refined
Δρmax, Δρmin (e Å3)0.17, 0.17

Computer programs: X-AREA (Stoe & Cie, 2002), X-AREA, X-RED (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996), WinGX (Farrugia, 1997) and PARST (Nardelli, 1995).

Selected geometric parameters (Å, º) top
F1—C11.3598 (19)N2—N31.3777 (19)
O1—C81.2314 (18)N3—C91.2975 (19)
N1—C71.2730 (19)N4—C91.3859 (18)
N1—N41.3878 (16)N4—C81.3890 (19)
N2—C81.3459 (19)
C7—N1—N4117.68 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2N···O1i0.861.972.799 (2)161
C7—H7···O10.932.192.893 (2)132
Symmetry code: (i) x2, y1, z+2.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds