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In the title compound, C17H19N5, the almost ideally planar triazole ring forms a dihedral angle of 75.1 (1)° with the benzene ring. There are inter­molecular π–π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805020143/ob6540sup1.cif
Contains datablocks General, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805020143/ob6540Isup2.hkl
Contains datablock I

CCDC reference: 282554

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.063
  • wR factor = 0.203
  • Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for C14 - C15 .. 6.16 su PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 .. N3 .. 2.67 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H4 .. N5 .. 2.69 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H162 .. N4 .. 2.74 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 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 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

(I) top
Crystal data top
C17H19N5F(000) = 1248.00
Mr = 293.37Dx = 1.196 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.7107 Å
Hall symbol: -C 2ycCell parameters from 10339 reflections
a = 17.9107 (8) Åθ = 2.2–27.5°
b = 11.2522 (3) ŵ = 0.08 mm1
c = 18.9011 (7) ÅT = 295 K
β = 121.181 (1)°Prism, colorless
V = 3258.9 (2) Å30.45 × 0.45 × 0.20 mm
Z = 8
Data collection top
Rigaku R-AXIS RAPID
diffractometer
Rint = 0.031
Detector resolution: 10.00 pixels mm-1θmax = 27.5°
ω scansh = 2323
16052 measured reflectionsk = 1414
3748 independent reflectionsl = 2324
2348 reflections with F2 > 2σ(F2)
Refinement top
Refinement on F2 w = 1/[0.0057Fo2 + σ(Fo2)]/(4Fo2)
R[F2 > 2σ(F2)] = 0.063(Δ/σ)max < 0.001
wR(F2) = 0.203Δρmax = 0.37 e Å3
S = 1.00Δρmin = 0.37 e Å3
3197 reflectionsExtinction correction: Larson (1970)
200 parametersExtinction coefficient: 184 (57)
H-atom parameters constrained
Special details top

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.7456 (1)0.1178 (1)0.7652 (1)0.0360 (4)
N20.7743 (1)0.0422 (2)0.7282 (1)0.0510 (6)
N30.8292 (1)0.2258 (2)0.7384 (1)0.0557 (6)
N40.2402 (1)0.0849 (2)0.5292 (2)0.0615 (7)
N50.2937 (2)0.3453 (2)0.5999 (1)0.0592 (7)
C10.5897 (1)0.0883 (2)0.7136 (1)0.0319 (5)
C20.5404 (1)0.0125 (2)0.6766 (1)0.0321 (5)
C30.4549 (1)0.0020 (2)0.6094 (1)0.0304 (5)
C40.4211 (1)0.1102 (2)0.5808 (1)0.0335 (5)
C50.4705 (1)0.2123 (2)0.6173 (1)0.0325 (5)
C60.5545 (1)0.2000 (2)0.6839 (1)0.0345 (5)
C70.6823 (1)0.0774 (2)0.7863 (1)0.0363 (5)
C80.8238 (2)0.1121 (2)0.7143 (2)0.0558 (8)
C90.7789 (1)0.2252 (2)0.7703 (1)0.0479 (6)
C100.4007 (1)0.1125 (2)0.5638 (1)0.0351 (5)
C110.3100 (1)0.0957 (2)0.5445 (1)0.0395 (6)
C120.3976 (2)0.1256 (3)0.4815 (2)0.0635 (9)
C130.4339 (2)0.2265 (2)0.6156 (2)0.0579 (7)
C140.4292 (1)0.3347 (2)0.5820 (1)0.0382 (5)
C150.3516 (2)0.3423 (2)0.5906 (1)0.0418 (6)
C160.3987 (2)0.3435 (2)0.4899 (2)0.0564 (8)
C170.4894 (2)0.4392 (2)0.6296 (2)0.0668 (8)
H20.56410.08730.69660.038*
H40.36430.11770.53630.038*
H60.58790.26740.70910.040*
H710.69330.00190.80240.040*
H720.68800.12310.82990.041*
H80.85320.08490.68890.071*
H90.76780.29130.79300.057*
H1210.34970.08450.44020.081*
H1220.39280.20560.46740.080*
H1230.44850.09470.48690.080*
H1310.47470.26300.60630.060*
H1320.38730.27790.60040.060*
H1330.45990.20780.67140.060*
H1610.44380.37300.48410.071*
H1620.35110.39450.46390.071*
H1630.38260.26860.46580.071*
H1710.48040.46230.67180.074*
H1720.47700.50250.59350.073*
H1730.54730.41630.65200.074*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0270 (9)0.0365 (9)0.0365 (9)0.0012 (7)0.0108 (7)0.0033 (7)
N20.051 (1)0.043 (1)0.069 (1)0.0026 (9)0.038 (1)0.0048 (9)
N30.048 (1)0.054 (1)0.067 (1)0.012 (1)0.031 (1)0.006 (1)
N40.032 (1)0.049 (1)0.092 (2)0.0049 (9)0.024 (1)0.016 (1)
N50.058 (1)0.057 (1)0.073 (2)0.015 (1)0.042 (1)0.006 (1)
C10.026 (1)0.035 (1)0.033 (1)0.0006 (8)0.0140 (8)0.0017 (8)
C20.031 (1)0.0281 (9)0.037 (1)0.0048 (7)0.0175 (9)0.0055 (8)
C30.028 (1)0.0277 (9)0.035 (1)0.0009 (7)0.0156 (8)0.0018 (7)
C40.027 (1)0.032 (1)0.036 (1)0.0020 (8)0.0126 (8)0.0008 (8)
C50.030 (1)0.029 (1)0.038 (1)0.0014 (8)0.0170 (8)0.0001 (8)
C60.031 (1)0.030 (1)0.040 (1)0.0039 (8)0.0162 (9)0.0020 (8)
C70.029 (1)0.040 (1)0.032 (1)0.0015 (8)0.0103 (8)0.0022 (8)
C80.050 (2)0.058 (1)0.069 (2)0.001 (1)0.038 (1)0.000 (1)
C90.042 (1)0.044 (1)0.055 (1)0.010 (1)0.023 (1)0.009 (1)
C100.031 (1)0.027 (1)0.044 (1)0.0009 (8)0.0173 (9)0.0038 (8)
C110.034 (1)0.030 (1)0.048 (1)0.0052 (8)0.0168 (9)0.0078 (8)
C120.070 (2)0.066 (2)0.063 (2)0.016 (1)0.041 (2)0.025 (1)
C130.038 (1)0.028 (1)0.082 (2)0.0019 (9)0.013 (1)0.000 (1)
C140.035 (1)0.027 (1)0.050 (1)0.0040 (8)0.020 (1)0.0042 (9)
C150.043 (1)0.031 (1)0.047 (1)0.0103 (9)0.020 (1)0.0055 (9)
C160.071 (2)0.045 (1)0.060 (1)0.021 (1)0.039 (1)0.022 (1)
C170.059 (2)0.028 (1)0.096 (2)0.001 (1)0.027 (2)0.002 (1)
Geometric parameters (Å, º) top
N1—N21.360 (3)C14—C161.534 (4)
N1—C71.455 (4)C14—C171.533 (3)
N1—C91.329 (3)C2—H20.9300
N2—C81.309 (4)C4—H40.9300
N3—C81.344 (4)C6—H60.9300
N3—C91.319 (5)C7—H710.9300
N4—C111.135 (4)C7—H720.9300
N5—C151.138 (5)C8—H80.9300
C1—C21.384 (3)C9—H90.9300
C1—C61.388 (3)C12—H1210.9300
C1—C71.516 (2)C12—H1220.9300
C2—C31.401 (2)C12—H1230.9300
C3—C41.384 (3)C13—H1310.9300
C3—C101.537 (3)C13—H1320.9300
C4—C51.395 (3)C13—H1330.9300
C5—C61.380 (2)C16—H1610.9300
C5—C141.543 (3)C16—H1620.9300
C10—C111.482 (4)C16—H1630.9300
C10—C121.535 (5)C17—H1710.9300
C10—C131.534 (3)C17—H1720.9300
C14—C151.483 (4)C17—H1730.9300
C7—N1—N2120.1 (2)N2—C8—H8121.9581
N1—N2—C8101.7 (2)N3—C8—H8121.8270
C9—N1—N2109.3 (2)N3—C9—H9124.4928
N1—C7—C1111.6 (2)C1—C2—H2120.0445
C9—N1—C7130.4 (2)C1—C6—H6119.6146
N1—C9—N3111.0 (2)C1—C7—H71108.7555
N2—C8—N3116.2 (3)C1—C7—H72108.9802
C9—N3—C8101.7 (3)H2—C2—C3119.8940
N4—C11—C10178.7 (2)C3—C4—H4119.1821
N5—C15—C14177.3 (2)H4—C4—C5119.3617
C6—C1—C2120.1 (2)C5—C6—H6119.6170
C7—C1—C2120.2 (2)H72—C7—H71109.4555
C1—C2—C3120.1 (2)C10—C12—H121109.6657
C7—C1—C6119.7 (2)C10—C12—H123109.3812
C1—C6—C5120.8 (2)C10—C12—H122109.3603
C2—C3—C10121.1 (2)C10—C13—H132109.4423
C2—C3—C4118.8 (2)C10—C13—H131109.3421
C10—C3—C4119.9 (1)C10—C13—H133109.6271
C3—C4—C5121.5 (2)H123—C12—H121109.4809
C3—C10—C11109.1 (2)H122—C12—H121109.4654
C3—C10—C12109.1 (2)H123—C12—H122109.4736
C3—C10—C13113.2 (1)H132—C13—H131109.4763
C4—C5—C6118.8 (2)H133—C13—H131109.4719
C4—C5—C14118.8 (1)H133—C13—H132109.4675
C14—C5—C6122.4 (2)C14—C16—H162109.1765
C5—C14—C15105.7 (2)C14—C16—H163109.5614
C5—C14—C16111.0 (2)C14—C16—H161109.6723
C5—C14—C17113.3 (2)C14—C17—H171109.6386
C12—C10—C11107.6 (2)C14—C17—H172109.2013
C13—C10—C11106.1 (2)C14—C17—H173109.5696
C13—C10—C12111.4 (2)H162—C16—H161109.4717
C16—C14—C15108.5 (2)H163—C16—H161109.4743
C17—C14—C15107.8 (2)H163—C16—H162109.4707
C17—C14—C16110.2 (2)H172—C17—H171109.4659
N1—C7—H71108.9729H173—C17—H171109.4728
N1—C7—H72109.0319H173—C17—H172109.4787
N1—C9—H9124.4760
C7—N1—N2—C8175.7 (2)C2—C1—C7—N1113.1 (3)
N2—N1—C7—C184.8 (2)C1—C2—C3—C40.3 (4)
N2—N1—C9—N30.1 (2)C2—C3—C4—C50.3 (4)
N1—N2—C8—N30.4 (3)C2—C3—C10—C11139.0 (2)
C9—N3—C8—N20.3 (3)C3—C4—C5—C60.7 (4)
C8—N3—C9—N10.1 (2)C4—C5—C6—C10.6 (4)
C6—C1—C2—C30.3 (4)C4—C5—C14—C1560.2 (3)
C2—C1—C6—C50.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···N3i0.932.683.580 (3)165
C4—H4···N5ii0.932.703.622 (3)174
C16—H162···N4ii0.932.743.573 (4)150
Symmetry codes: (i) x+3/2, y1/2, z+3/2; (ii) x+1/2, y+1/2, z+1.
 

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