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In the title compound, C14H15N5O, the benzene and triazole rings are almost perpendicular and the dihedral angle between the pyrazole and triazole rings is 79.63 (3)°. There are some weak inter­molecular C—H...O hydrogen-bond inter­actions in the crystal structure, which provide stabilization.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805031594/dn6256sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805031594/dn6256Isup2.hkl
Contains datablock I

CCDC reference: 289711

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C)= 0.003 Å
  • R factor = 0.043
  • wR factor = 0.121
  • Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

Computing details top

Data collection: SMART (Bruker, 1998); 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: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

1-(4,5-Dihydro-3-p-tolyl-1H-pyrazol-1-yl)-2-(1,2,4-triazol-1-yl)ethanone top
Crystal data top
C14H15N5OF(000) = 568
Mr = 269.31Dx = 1.315 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yb cCell parameters from 1785 reflections
a = 5.2398 (10) Åθ = 2.3–25.9°
b = 17.978 (3) ŵ = 0.09 mm1
c = 14.476 (3) ÅT = 294 K
β = 94.064 (3)°Block, white
V = 1360.2 (4) Å30.22 × 0.16 × 0.14 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
2772 independent reflections
Radiation source: fine-focus sealed tube1619 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
φ and ω scansθmax = 26.4°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 63
Tmin = 0.970, Tmax = 0.988k = 2222
7599 measured reflectionsl = 1717
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0512P)2 + 0.1972P]
where P = (Fo2 + 2Fc2)/3
2772 reflections(Δ/σ)max = 0.001
182 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = 0.15 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
O10.1837 (3)0.69414 (8)0.24701 (9)0.0601 (4)
N10.3109 (3)0.66449 (9)0.10775 (10)0.0472 (4)
N20.4825 (3)0.62748 (9)0.05399 (10)0.0465 (4)
N30.5793 (3)0.61871 (9)0.34080 (10)0.0465 (4)
N40.4239 (4)0.58073 (11)0.39461 (13)0.0718 (6)
N50.7100 (4)0.64886 (12)0.48184 (12)0.0701 (6)
C10.1286 (4)0.71127 (13)0.05248 (14)0.0584 (6)
H1A0.13660.76260.07330.070*
H1B0.04510.69310.05490.070*
C20.2213 (4)0.70350 (11)0.04431 (13)0.0484 (5)
H2A0.08590.68540.08780.058*
H2B0.28420.75050.06640.058*
C30.4336 (3)0.64747 (10)0.03052 (12)0.0398 (5)
C40.5840 (3)0.61955 (10)0.10463 (12)0.0402 (4)
C50.5685 (4)0.65408 (11)0.19055 (12)0.0493 (5)
H50.45400.69310.20200.059*
C60.7209 (4)0.63125 (12)0.25939 (13)0.0534 (5)
H60.70920.65590.31600.064*
C70.8900 (4)0.57274 (11)0.24616 (13)0.0482 (5)
C80.9005 (4)0.53738 (11)0.16096 (13)0.0547 (6)
H81.01110.49730.15050.066*
C90.7522 (4)0.55974 (11)0.09124 (13)0.0504 (5)
H90.76420.53480.03480.060*
C101.0529 (4)0.54823 (14)0.32189 (14)0.0663 (6)
H10A1.02540.58090.37410.099*
H10B1.00750.49840.34030.099*
H10C1.22990.54970.29970.099*
C110.3320 (4)0.66105 (11)0.20006 (12)0.0441 (5)
C120.5529 (4)0.61390 (12)0.24106 (12)0.0520 (5)
H12A0.52480.56240.22300.062*
H12B0.71040.63040.21620.062*
C130.7448 (4)0.65773 (12)0.39366 (14)0.0572 (6)
H130.87080.68790.37120.069*
C140.5131 (5)0.60126 (14)0.47761 (16)0.0722 (7)
H140.44340.58370.53070.087*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0520 (9)0.0814 (10)0.0476 (8)0.0084 (8)0.0101 (7)0.0122 (7)
N10.0435 (10)0.0615 (10)0.0372 (9)0.0087 (8)0.0061 (8)0.0015 (8)
N20.0462 (10)0.0551 (10)0.0384 (9)0.0057 (8)0.0050 (8)0.0037 (7)
N30.0473 (10)0.0566 (10)0.0360 (9)0.0027 (8)0.0053 (8)0.0028 (8)
N40.0836 (14)0.0789 (13)0.0544 (12)0.0293 (12)0.0165 (11)0.0010 (10)
N50.0829 (15)0.0845 (14)0.0418 (11)0.0078 (12)0.0037 (10)0.0006 (9)
C10.0462 (12)0.0780 (15)0.0510 (13)0.0124 (11)0.0032 (10)0.0007 (11)
C20.0413 (11)0.0578 (12)0.0463 (11)0.0019 (10)0.0029 (9)0.0014 (9)
C30.0363 (11)0.0439 (11)0.0389 (10)0.0062 (9)0.0006 (8)0.0017 (8)
C40.0389 (11)0.0452 (11)0.0362 (10)0.0057 (9)0.0009 (8)0.0015 (8)
C50.0469 (12)0.0596 (13)0.0410 (11)0.0061 (10)0.0002 (10)0.0009 (9)
C60.0562 (13)0.0679 (14)0.0360 (11)0.0003 (11)0.0022 (10)0.0038 (10)
C70.0467 (12)0.0572 (12)0.0407 (11)0.0072 (10)0.0041 (9)0.0076 (9)
C80.0618 (14)0.0505 (12)0.0524 (12)0.0111 (10)0.0082 (11)0.0035 (10)
C90.0617 (14)0.0486 (11)0.0413 (11)0.0045 (10)0.0066 (10)0.0038 (9)
C100.0624 (15)0.0848 (16)0.0529 (13)0.0039 (13)0.0130 (11)0.0114 (12)
C110.0394 (11)0.0529 (12)0.0406 (11)0.0043 (9)0.0067 (9)0.0084 (9)
C120.0524 (13)0.0671 (13)0.0368 (11)0.0064 (11)0.0051 (9)0.0055 (9)
C130.0539 (14)0.0690 (14)0.0479 (13)0.0087 (11)0.0029 (11)0.0021 (11)
C140.097 (2)0.0794 (17)0.0422 (14)0.0027 (15)0.0173 (13)0.0090 (12)
Geometric parameters (Å, º) top
O1—C111.222 (2)C4—C91.395 (3)
N1—C111.335 (2)C5—C61.383 (3)
N1—N21.399 (2)C5—H50.9300
N1—C11.467 (2)C6—C71.380 (3)
N2—C31.283 (2)C6—H60.9300
N3—C131.317 (2)C7—C81.385 (3)
N3—N41.351 (2)C7—C101.502 (3)
N3—C121.443 (2)C8—C91.377 (3)
N4—C141.311 (3)C8—H80.9300
N5—C131.312 (2)C9—H90.9300
N5—C141.338 (3)C10—H10A0.9600
C1—C21.521 (3)C10—H10B0.9600
C1—H1A0.9700C10—H10C0.9600
C1—H1B0.9700C11—C121.521 (3)
C2—C31.503 (3)C12—H12A0.9700
C2—H2A0.9700C12—H12B0.9700
C2—H2B0.9700C13—H130.9300
C3—C41.464 (2)C14—H140.9300
C4—C51.387 (2)
C11—N1—N2121.61 (16)C5—C6—H6119.2
C11—N1—C1125.26 (16)C6—C7—C8117.25 (18)
N2—N1—C1112.88 (14)C6—C7—C10120.98 (18)
C3—N2—N1107.71 (15)C8—C7—C10121.77 (19)
C13—N3—N4109.45 (16)C9—C8—C7122.01 (19)
C13—N3—C12128.72 (18)C9—C8—H8119.0
N4—N3—C12121.82 (17)C7—C8—H8119.0
C14—N4—N3101.27 (18)C8—C9—C4120.46 (18)
C13—N5—C14101.12 (18)C8—C9—H9119.8
N1—C1—C2102.23 (15)C4—C9—H9119.8
N1—C1—H1A111.3C7—C10—H10A109.5
C2—C1—H1A111.3C7—C10—H10B109.5
N1—C1—H1B111.3H10A—C10—H10B109.5
C2—C1—H1B111.3C7—C10—H10C109.5
H1A—C1—H1B109.2H10A—C10—H10C109.5
C3—C2—C1102.75 (15)H10B—C10—H10C109.5
C3—C2—H2A111.2O1—C11—N1121.57 (18)
C1—C2—H2A111.2O1—C11—C12123.39 (17)
C3—C2—H2B111.2N1—C11—C12115.04 (17)
C1—C2—H2B111.2N3—C12—C11111.93 (16)
H2A—C2—H2B109.1N3—C12—H12A109.2
N2—C3—C4121.39 (17)C11—C12—H12A109.2
N2—C3—C2114.21 (16)N3—C12—H12B109.2
C4—C3—C2124.33 (16)C11—C12—H12B109.2
C5—C4—C9117.76 (17)H12A—C12—H12B107.9
C5—C4—C3120.21 (17)N5—C13—N3111.7 (2)
C9—C4—C3122.00 (16)N5—C13—H13124.2
C6—C5—C4120.87 (19)N3—C13—H13124.2
C6—C5—H5119.6N4—C14—N5116.5 (2)
C4—C5—H5119.6N4—C14—H14121.8
C7—C6—C5121.62 (18)N5—C14—H14121.8
C7—C6—H6119.2
C11—N1—N2—C3172.80 (17)C5—C6—C7—C10179.53 (19)
C1—N1—N2—C31.8 (2)C6—C7—C8—C90.9 (3)
C13—N3—N4—C140.1 (2)C10—C7—C8—C9179.82 (19)
C12—N3—N4—C14179.73 (19)C7—C8—C9—C40.1 (3)
C11—N1—C1—C2170.26 (18)C5—C4—C9—C81.3 (3)
N2—N1—C1—C24.1 (2)C3—C4—C9—C8176.62 (17)
N1—C1—C2—C34.5 (2)N2—N1—C11—O1179.10 (16)
N1—N2—C3—C4178.77 (15)C1—N1—C11—O15.2 (3)
N1—N2—C3—C21.5 (2)N2—N1—C11—C120.5 (3)
C1—C2—C3—N24.0 (2)C1—N1—C11—C12174.37 (18)
C1—C2—C3—C4178.84 (17)C13—N3—C12—C11101.8 (2)
N2—C3—C4—C5165.09 (18)N4—N3—C12—C1178.0 (2)
C2—C3—C4—C511.9 (3)O1—C11—C12—N35.3 (3)
N2—C3—C4—C912.8 (3)N1—C11—C12—N3174.23 (17)
C2—C3—C4—C9170.23 (18)C14—N5—C13—N30.5 (3)
C9—C4—C5—C62.0 (3)N4—N3—C13—N50.4 (3)
C3—C4—C5—C6176.00 (17)C12—N3—C13—N5179.43 (19)
C4—C5—C6—C71.2 (3)N3—N4—C14—N50.2 (3)
C5—C6—C7—C80.3 (3)C13—N5—C14—N40.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···O1i0.932.553.474 (3)171
C13—H13···O1ii0.932.523.304 (3)142
Symmetry codes: (i) x, y+3/2, z1/2; (ii) x+1, y, z.
 

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