1-(4,5-Dihydro-3-p-tolyl-1H-pyrazol-1-yl)-2-(1,2,4-triazol-1-yl)ethanone

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.

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

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Computing details

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

Crystal data

C14H15N5O	F(000) = 568
Mr = 269.31	Dx = 1.315 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yb c	Cell parameters from 1785 reflections
a = 5.2398 (10) Å	θ = 2.3–25.9°
b = 17.978 (3) Å	µ = 0.09 mm^−1
c = 14.476 (3) Å	T = 294 K
β = 94.064 (3)°	Block, white
V = 1360.2 (4) Å^3	0.22 × 0.16 × 0.14 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	2772 independent reflections
Radiation source: fine-focus sealed tube	1619 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
φ and ω scans	θmax = 26.4°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→3
Tmin = 0.970, Tmax = 0.988	k = −22→22
7599 measured reflections	l = −17→17

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.121	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0512P)^2 + 0.1972P] where P = (Fo^2 + 2Fc^2)/3
2772 reflections	(Δ/σ)max = 0.001
182 parameters	Δρmax = 0.15 e Å^−3
0 restraints	Δρmin = −0.15 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.1837 (3)	0.69414 (8)	0.24701 (9)	0.0601 (4)
N1	0.3109 (3)	0.66449 (9)	0.10775 (10)	0.0472 (4)
N2	0.4825 (3)	0.62748 (9)	0.05399 (10)	0.0465 (4)
N3	0.5793 (3)	0.61871 (9)	0.34080 (10)	0.0465 (4)
N4	0.4239 (4)	0.58073 (11)	0.39461 (13)	0.0718 (6)
N5	0.7100 (4)	0.64886 (12)	0.48184 (12)	0.0701 (6)
C1	0.1286 (4)	0.71127 (13)	0.05248 (14)	0.0584 (6)
H1A	0.1366	0.7626	0.0733	0.070*
H1B	−0.0451	0.6931	0.0549	0.070*
C2	0.2213 (4)	0.70350 (11)	−0.04431 (13)	0.0484 (5)
H2A	0.0859	0.6854	−0.0878	0.058*
H2B	0.2842	0.7505	−0.0664	0.058*
C3	0.4336 (3)	0.64747 (10)	−0.03052 (12)	0.0398 (5)
C4	0.5840 (3)	0.61955 (10)	−0.10463 (12)	0.0402 (4)
C5	0.5685 (4)	0.65408 (11)	−0.19055 (12)	0.0493 (5)
H5	0.4540	0.6931	−0.2020	0.059*
C6	0.7209 (4)	0.63125 (12)	−0.25939 (13)	0.0534 (5)
H6	0.7092	0.6559	−0.3160	0.064*
C7	0.8900 (4)	0.57274 (11)	−0.24616 (13)	0.0482 (5)
C8	0.9005 (4)	0.53738 (11)	−0.16096 (13)	0.0547 (6)
H8	1.0111	0.4973	−0.1505	0.066*
C9	0.7522 (4)	0.55974 (11)	−0.09124 (13)	0.0504 (5)
H9	0.7642	0.5348	−0.0348	0.060*
C10	1.0529 (4)	0.54823 (14)	−0.32189 (14)	0.0663 (6)
H10A	1.0254	0.5809	−0.3741	0.099*
H10B	1.0075	0.4984	−0.3403	0.099*
H10C	1.2299	0.5497	−0.2997	0.099*
C11	0.3320 (4)	0.66105 (11)	0.20006 (12)	0.0441 (5)
C12	0.5529 (4)	0.61390 (12)	0.24106 (12)	0.0520 (5)
H12A	0.5248	0.5624	0.2230	0.062*
H12B	0.7104	0.6304	0.2162	0.062*
C13	0.7448 (4)	0.65773 (12)	0.39366 (14)	0.0572 (6)
H13	0.8708	0.6879	0.3712	0.069*
C14	0.5131 (5)	0.60126 (14)	0.47761 (16)	0.0722 (7)
H14	0.4434	0.5837	0.5307	0.087*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0520 (9)	0.0814 (10)	0.0476 (8)	0.0084 (8)	0.0101 (7)	−0.0122 (7)
N1	0.0435 (10)	0.0615 (10)	0.0372 (9)	0.0087 (8)	0.0061 (8)	−0.0015 (8)
N2	0.0462 (10)	0.0551 (10)	0.0384 (9)	0.0057 (8)	0.0050 (8)	−0.0037 (7)
N3	0.0473 (10)	0.0566 (10)	0.0360 (9)	−0.0027 (8)	0.0053 (8)	−0.0028 (8)
N4	0.0836 (14)	0.0789 (13)	0.0544 (12)	−0.0293 (12)	0.0165 (11)	0.0010 (10)
N5	0.0829 (15)	0.0845 (14)	0.0418 (11)	−0.0078 (12)	−0.0037 (10)	−0.0006 (9)
C1	0.0462 (12)	0.0780 (15)	0.0510 (13)	0.0124 (11)	0.0032 (10)	0.0007 (11)
C2	0.0413 (11)	0.0578 (12)	0.0463 (11)	0.0019 (10)	0.0029 (9)	0.0014 (9)
C3	0.0363 (11)	0.0439 (11)	0.0389 (10)	−0.0062 (9)	0.0006 (8)	−0.0017 (8)
C4	0.0389 (11)	0.0452 (11)	0.0362 (10)	−0.0057 (9)	0.0009 (8)	−0.0015 (8)
C5	0.0469 (12)	0.0596 (13)	0.0410 (11)	0.0061 (10)	0.0002 (10)	0.0009 (9)
C6	0.0562 (13)	0.0679 (14)	0.0360 (11)	0.0003 (11)	0.0022 (10)	0.0038 (10)
C7	0.0467 (12)	0.0572 (12)	0.0407 (11)	−0.0072 (10)	0.0041 (9)	−0.0076 (9)
C8	0.0618 (14)	0.0505 (12)	0.0524 (12)	0.0111 (10)	0.0082 (11)	−0.0035 (10)
C9	0.0617 (14)	0.0486 (11)	0.0413 (11)	0.0045 (10)	0.0066 (10)	0.0038 (9)
C10	0.0624 (15)	0.0848 (16)	0.0529 (13)	0.0039 (13)	0.0130 (11)	−0.0114 (12)
C11	0.0394 (11)	0.0529 (12)	0.0406 (11)	−0.0043 (9)	0.0067 (9)	−0.0084 (9)
C12	0.0524 (13)	0.0671 (13)	0.0368 (11)	0.0064 (11)	0.0051 (9)	−0.0055 (9)
C13	0.0539 (14)	0.0690 (14)	0.0479 (13)	−0.0087 (11)	−0.0029 (11)	0.0021 (11)
C14	0.097 (2)	0.0794 (17)	0.0422 (14)	−0.0027 (15)	0.0173 (13)	0.0090 (12)

Geometric parameters (Å, º)

O1—C11	1.222 (2)	C4—C9	1.395 (3)
N1—C11	1.335 (2)	C5—C6	1.383 (3)
N1—N2	1.399 (2)	C5—H5	0.9300
N1—C1	1.467 (2)	C6—C7	1.380 (3)
N2—C3	1.283 (2)	C6—H6	0.9300
N3—C13	1.317 (2)	C7—C8	1.385 (3)
N3—N4	1.351 (2)	C7—C10	1.502 (3)
N3—C12	1.443 (2)	C8—C9	1.377 (3)
N4—C14	1.311 (3)	C8—H8	0.9300
N5—C13	1.312 (2)	C9—H9	0.9300
N5—C14	1.338 (3)	C10—H10A	0.9600
C1—C2	1.521 (3)	C10—H10B	0.9600
C1—H1A	0.9700	C10—H10C	0.9600
C1—H1B	0.9700	C11—C12	1.521 (3)
C2—C3	1.503 (3)	C12—H12A	0.9700
C2—H2A	0.9700	C12—H12B	0.9700
C2—H2B	0.9700	C13—H13	0.9300
C3—C4	1.464 (2)	C14—H14	0.9300
C4—C5	1.387 (2)
C11—N1—N2	121.61 (16)	C5—C6—H6	119.2
C11—N1—C1	125.26 (16)	C6—C7—C8	117.25 (18)
N2—N1—C1	112.88 (14)	C6—C7—C10	120.98 (18)
C3—N2—N1	107.71 (15)	C8—C7—C10	121.77 (19)
C13—N3—N4	109.45 (16)	C9—C8—C7	122.01 (19)
C13—N3—C12	128.72 (18)	C9—C8—H8	119.0
N4—N3—C12	121.82 (17)	C7—C8—H8	119.0
C14—N4—N3	101.27 (18)	C8—C9—C4	120.46 (18)
C13—N5—C14	101.12 (18)	C8—C9—H9	119.8
N1—C1—C2	102.23 (15)	C4—C9—H9	119.8
N1—C1—H1A	111.3	C7—C10—H10A	109.5
C2—C1—H1A	111.3	C7—C10—H10B	109.5
N1—C1—H1B	111.3	H10A—C10—H10B	109.5
C2—C1—H1B	111.3	C7—C10—H10C	109.5
H1A—C1—H1B	109.2	H10A—C10—H10C	109.5
C3—C2—C1	102.75 (15)	H10B—C10—H10C	109.5
C3—C2—H2A	111.2	O1—C11—N1	121.57 (18)
C1—C2—H2A	111.2	O1—C11—C12	123.39 (17)
C3—C2—H2B	111.2	N1—C11—C12	115.04 (17)
C1—C2—H2B	111.2	N3—C12—C11	111.93 (16)
H2A—C2—H2B	109.1	N3—C12—H12A	109.2
N2—C3—C4	121.39 (17)	C11—C12—H12A	109.2
N2—C3—C2	114.21 (16)	N3—C12—H12B	109.2
C4—C3—C2	124.33 (16)	C11—C12—H12B	109.2
C5—C4—C9	117.76 (17)	H12A—C12—H12B	107.9
C5—C4—C3	120.21 (17)	N5—C13—N3	111.7 (2)
C9—C4—C3	122.00 (16)	N5—C13—H13	124.2
C6—C5—C4	120.87 (19)	N3—C13—H13	124.2
C6—C5—H5	119.6	N4—C14—N5	116.5 (2)
C4—C5—H5	119.6	N4—C14—H14	121.8
C7—C6—C5	121.62 (18)	N5—C14—H14	121.8
C7—C6—H6	119.2
C11—N1—N2—C3	−172.80 (17)	C5—C6—C7—C10	179.53 (19)
C1—N1—N2—C3	1.8 (2)	C6—C7—C8—C9	−0.9 (3)
C13—N3—N4—C14	0.1 (2)	C10—C7—C8—C9	179.82 (19)
C12—N3—N4—C14	−179.73 (19)	C7—C8—C9—C4	0.1 (3)
C11—N1—C1—C2	170.26 (18)	C5—C4—C9—C8	1.3 (3)
N2—N1—C1—C2	−4.1 (2)	C3—C4—C9—C8	−176.62 (17)
N1—C1—C2—C3	4.5 (2)	N2—N1—C11—O1	179.10 (16)
N1—N2—C3—C4	178.77 (15)	C1—N1—C11—O1	5.2 (3)
N1—N2—C3—C2	1.5 (2)	N2—N1—C11—C12	−0.5 (3)
C1—C2—C3—N2	−4.0 (2)	C1—N1—C11—C12	−174.37 (18)
C1—C2—C3—C4	178.84 (17)	C13—N3—C12—C11	−101.8 (2)
N2—C3—C4—C5	−165.09 (18)	N4—N3—C12—C11	78.0 (2)
C2—C3—C4—C5	11.9 (3)	O1—C11—C12—N3	−5.3 (3)
N2—C3—C4—C9	12.8 (3)	N1—C11—C12—N3	174.23 (17)
C2—C3—C4—C9	−170.23 (18)	C14—N5—C13—N3	0.5 (3)
C9—C4—C5—C6	−2.0 (3)	N4—N3—C13—N5	−0.4 (3)
C3—C4—C5—C6	176.00 (17)	C12—N3—C13—N5	179.43 (19)
C4—C5—C6—C7	1.2 (3)	N3—N4—C14—N5	0.2 (3)
C5—C6—C7—C8	0.3 (3)	C13—N5—C14—N4	−0.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1^i	0.93	2.55	3.474 (3)	171
C13—H13···O1^ii	0.93	2.52	3.304 (3)	142

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x+1, y, z.