(Z)-1-(2,4-Dimethyl-phen-yl)-3-phenyl-2-(1H-1,2,4-triazol-1-yl)prop-2-en-1-one.

In the title compound, C(19)H(17)N(3)O, the triazole and benzene rings adopt a Z configuration with respect to the C=C bond. The phenyl and benzene rings form dihedral angles of 66.20 (9) and 14.36 (9)°, respectively, with the triazole ring. The dihedral angle between the phenyl and benzene rings is 52.64 (8)°.

Related literature

For the synthesis, see: Wang et al. (2009 ▶). For the pharmacological activity of triazole derivatives, see: Zhou & Wang (2012 ▶). For related structures, see: Wang et al. (2009 ▶); Yan et al. (2009 ▶).

Experimental

Crystal data

C19H17N3O

M = 303.36

Monoclinic,

a = 12.8499 (3) Å

b = 7.8836 (2) Å

c = 16.5274 (4) Å

β = 108.376 (1)°

V = 1588.91 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.20 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.984, T max = 0.986

11768 measured reflections

2796 independent reflections

2369 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.113

S = 1.04

2796 reflections

215 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.15 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812001390/lh5401sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812001390/lh5401Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812001390/lh5401Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C19H17N3O	F(000) = 640
Mr = 303.36	Dx = 1.268 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4934 reflections
a = 12.8499 (3) Å	θ = 2.4–27.1°
b = 7.8836 (2) Å	µ = 0.08 mm−1
c = 16.5274 (4) Å	T = 296 K
β = 108.376 (1)°	Block, colorless
V = 1588.91 (7) Å3	0.20 × 0.20 × 0.18 mm
Z = 4

Bruker SMART CCD diffractometer	2796 independent reflections
Radiation source: fine-focus sealed tube	2369 reflections with I > 2σ(I)
graphite	Rint = 0.025
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→9
Tmin = 0.984, Tmax = 0.986	k = −8→9
11768 measured reflections	l = −17→19

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.113	w = 1/[σ2(Fo2) + (0.0517P)2 + 0.3715P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.004
2796 reflections	Δρmax = 0.18 e Å−3
215 parameters	Δρmin = −0.15 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.017 (2)

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.

	x	y	z	Uiso*/Ueq
C1	0.20259 (13)	1.1290 (2)	0.85885 (11)	0.0604 (5)
H1	0.1666	1.2043	0.8842	0.072*
C2	0.23209 (14)	0.9674 (3)	0.77106 (11)	0.0636 (5)
H2	0.2254	0.9031	0.7225	0.076*
C3	0.29220 (13)	0.6718 (2)	0.94192 (10)	0.0531 (4)
H3	0.2511	0.7004	0.8865	0.064*
C4	0.24256 (14)	0.5912 (2)	0.99443 (12)	0.0634 (5)
H4	0.1685	0.5637	0.9736	0.076*
C5	0.30203 (15)	0.5514 (2)	1.07733 (11)	0.0615 (5)
H5	0.2679	0.4990	1.1126	0.074*
C6	0.41158 (15)	0.5892 (2)	1.10754 (10)	0.0578 (4)
H6	0.4518	0.5634	1.1636	0.069*
C7	0.46229 (13)	0.6653 (2)	1.05485 (9)	0.0479 (4)
H7	0.5372	0.6870	1.0753	0.057*
C8	0.40332 (11)	0.71002 (18)	0.97182 (9)	0.0413 (3)
C9	0.46292 (12)	0.78548 (19)	0.91780 (9)	0.0428 (4)
C10	0.42801 (11)	0.89791 (19)	0.85496 (9)	0.0417 (3)
C11	0.48890 (13)	0.9480 (2)	0.79522 (10)	0.0486 (4)
C12	0.60794 (12)	0.90705 (19)	0.81731 (9)	0.0450 (4)
C13	0.67846 (13)	0.9510 (2)	0.89704 (10)	0.0511 (4)
H13	0.6502	1.0017	0.9365	0.061*
C14	0.78937 (13)	0.9210 (2)	0.91891 (11)	0.0566 (4)
H14	0.8351	0.9543	0.9723	0.068*
C15	0.83373 (13)	0.8419 (2)	0.86257 (11)	0.0543 (4)
C16	0.76298 (13)	0.7989 (2)	0.78301 (10)	0.0531 (4)
H16	0.7918	0.7458	0.7446	0.064*
C17	0.65123 (12)	0.8313 (2)	0.75783 (10)	0.0481 (4)
C18	0.58064 (16)	0.7803 (3)	0.67006 (11)	0.0724 (6)
H18A	0.6255	0.7291	0.6400	0.109*
H18B	0.5449	0.8788	0.6396	0.109*
H18C	0.5264	0.7003	0.6746	0.109*
C19	0.95482 (15)	0.8037 (3)	0.88741 (15)	0.0825 (6)
H19A	0.9910	0.8916	0.8663	0.124*
H19B	0.9656	0.6968	0.8633	0.124*
H19C	0.9849	0.7983	0.9484	0.124*
H1M	0.5369 (13)	0.746 (2)	0.9311 (9)	0.045 (4)*
N1	0.15299 (12)	1.0603 (2)	0.78249 (9)	0.0674 (4)
N2	0.30462 (10)	1.08424 (18)	0.89592 (8)	0.0542 (4)
N3	0.32284 (9)	0.97702 (16)	0.83766 (7)	0.0434 (3)
O1	0.43871 (10)	1.0182 (2)	0.72867 (8)	0.0757 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0483 (9)	0.0687 (12)	0.0681 (10)	0.0169 (8)	0.0240 (8)	0.0059 (9)
C2	0.0531 (10)	0.0799 (13)	0.0503 (9)	0.0104 (9)	0.0054 (7)	−0.0035 (8)
C3	0.0446 (9)	0.0601 (10)	0.0544 (9)	−0.0009 (8)	0.0151 (7)	0.0054 (8)
C4	0.0486 (10)	0.0656 (12)	0.0804 (12)	−0.0063 (8)	0.0267 (9)	0.0067 (9)
C5	0.0705 (12)	0.0555 (10)	0.0703 (11)	0.0024 (9)	0.0390 (9)	0.0125 (8)
C6	0.0705 (12)	0.0536 (10)	0.0511 (9)	0.0068 (8)	0.0219 (8)	0.0097 (7)
C7	0.0460 (9)	0.0442 (9)	0.0527 (8)	0.0036 (7)	0.0144 (7)	0.0023 (7)
C8	0.0418 (8)	0.0375 (8)	0.0479 (8)	0.0051 (6)	0.0188 (6)	0.0002 (6)
C9	0.0380 (8)	0.0447 (8)	0.0482 (8)	0.0046 (7)	0.0174 (6)	−0.0012 (6)
C10	0.0368 (7)	0.0458 (8)	0.0449 (7)	0.0032 (6)	0.0166 (6)	−0.0011 (6)
C11	0.0487 (9)	0.0509 (9)	0.0509 (8)	0.0026 (7)	0.0225 (7)	0.0035 (7)
C12	0.0467 (8)	0.0428 (8)	0.0525 (8)	−0.0021 (7)	0.0259 (7)	0.0016 (7)
C13	0.0521 (9)	0.0533 (10)	0.0552 (9)	−0.0002 (7)	0.0272 (7)	−0.0055 (7)
C14	0.0488 (9)	0.0617 (11)	0.0599 (9)	−0.0061 (8)	0.0182 (7)	−0.0072 (8)
C15	0.0474 (9)	0.0499 (10)	0.0720 (10)	−0.0020 (7)	0.0280 (8)	−0.0005 (8)
C16	0.0565 (10)	0.0478 (9)	0.0672 (10)	−0.0023 (8)	0.0372 (8)	−0.0056 (8)
C17	0.0507 (9)	0.0455 (9)	0.0561 (9)	−0.0066 (7)	0.0284 (7)	−0.0030 (7)
C18	0.0682 (12)	0.0892 (15)	0.0663 (11)	−0.0097 (10)	0.0308 (9)	−0.0223 (10)
C19	0.0525 (11)	0.0907 (16)	0.1073 (16)	0.0077 (11)	0.0292 (11)	−0.0055 (13)
N1	0.0491 (8)	0.0839 (11)	0.0649 (9)	0.0173 (8)	0.0117 (7)	0.0101 (8)
N2	0.0462 (8)	0.0604 (9)	0.0585 (8)	0.0086 (6)	0.0201 (6)	−0.0077 (6)
N3	0.0397 (7)	0.0489 (7)	0.0427 (6)	0.0051 (5)	0.0145 (5)	0.0015 (5)
O1	0.0634 (8)	0.1056 (11)	0.0651 (8)	0.0179 (7)	0.0302 (6)	0.0344 (7)

C1—N2	1.308 (2)	C10—C11	1.4933 (19)
C1—N1	1.336 (2)	C11—O1	1.2186 (18)
C1—H1	0.9300	C11—C12	1.492 (2)
C2—N1	1.314 (2)	C12—C13	1.387 (2)
C2—N3	1.330 (2)	C12—C17	1.406 (2)
C2—H2	0.9300	C13—C14	1.376 (2)
C3—C4	1.383 (2)	C13—H13	0.9300
C3—C8	1.389 (2)	C14—C15	1.384 (2)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.378 (2)	C15—C16	1.384 (2)
C4—H4	0.9300	C15—C19	1.509 (2)
C5—C6	1.370 (2)	C16—C17	1.387 (2)
C5—H5	0.9300	C16—H16	0.9300
C6—C7	1.379 (2)	C17—C18	1.503 (2)
C6—H6	0.9300	C18—H18A	0.9600
C7—C8	1.388 (2)	C18—H18B	0.9600
C7—H7	0.9300	C18—H18C	0.9600
C8—C9	1.4727 (19)	C19—H19A	0.9600
C9—C10	1.331 (2)	C19—H19B	0.9600
C9—H1M	0.958 (15)	C19—H19C	0.9600
C10—N3	1.4330 (18)	N2—N3	1.3560 (17)
N2—C1—N1	116.25 (15)	C13—C12—C11	119.40 (13)
N2—C1—H1	121.9	C17—C12—C11	121.46 (14)
N1—C1—H1	121.9	C14—C13—C12	121.27 (14)
N1—C2—N3	111.45 (16)	C14—C13—H13	119.4
N1—C2—H2	124.3	C12—C13—H13	119.4
N3—C2—H2	124.3	C13—C14—C15	120.85 (15)
C4—C3—C8	120.15 (15)	C13—C14—H14	119.6
C4—C3—H3	119.9	C15—C14—H14	119.6
C8—C3—H3	119.9	C14—C15—C16	117.57 (15)
C5—C4—C3	120.50 (16)	C14—C15—C19	120.99 (16)
C5—C4—H4	119.7	C16—C15—C19	121.44 (16)
C3—C4—H4	119.7	C15—C16—C17	123.21 (14)
C6—C5—C4	119.79 (15)	C15—C16—H16	118.4
C6—C5—H5	120.1	C17—C16—H16	118.4
C4—C5—H5	120.1	C16—C17—C12	117.96 (14)
C5—C6—C7	120.03 (15)	C16—C17—C18	119.53 (14)
C5—C6—H6	120.0	C12—C17—C18	122.48 (14)
C7—C6—H6	120.0	C17—C18—H18A	109.5
C6—C7—C8	121.04 (15)	C17—C18—H18B	109.5
C6—C7—H7	119.5	H18A—C18—H18B	109.5
C8—C7—H7	119.5	C17—C18—H18C	109.5
C7—C8—C3	118.45 (13)	H18A—C18—H18C	109.5
C7—C8—C9	118.42 (13)	H18B—C18—H18C	109.5
C3—C8—C9	123.01 (13)	C15—C19—H19A	109.5
C10—C9—C8	129.07 (14)	C15—C19—H19B	109.5
C10—C9—H1M	117.6 (9)	H19A—C19—H19B	109.5
C8—C9—H1M	113.3 (9)	C15—C19—H19C	109.5
C9—C10—N3	120.68 (13)	H19A—C19—H19C	109.5
C9—C10—C11	125.02 (13)	H19B—C19—H19C	109.5
N3—C10—C11	114.25 (12)	C2—N1—C1	101.62 (14)
O1—C11—C12	121.95 (13)	C1—N2—N3	101.96 (13)
O1—C11—C10	118.58 (14)	C2—N3—N2	108.70 (13)
C12—C11—C10	119.45 (13)	C2—N3—C10	131.78 (13)
C13—C12—C17	119.09 (14)	N2—N3—C10	119.52 (11)
C8—C3—C4—C5	1.4 (3)	C12—C13—C14—C15	−1.6 (3)
C3—C4—C5—C6	−1.1 (3)	C13—C14—C15—C16	1.8 (3)
C4—C5—C6—C7	−0.6 (3)	C13—C14—C15—C19	−178.00 (17)
C5—C6—C7—C8	2.2 (3)	C14—C15—C16—C17	0.0 (3)
C6—C7—C8—C3	−1.9 (2)	C19—C15—C16—C17	179.80 (16)
C6—C7—C8—C9	−177.89 (14)	C15—C16—C17—C12	−1.9 (2)
C4—C3—C8—C7	0.1 (2)	C15—C16—C17—C18	179.96 (16)
C4—C3—C8—C9	175.91 (15)	C13—C12—C17—C16	2.1 (2)
C7—C8—C9—C10	−149.02 (16)	C11—C12—C17—C16	179.33 (14)
C3—C8—C9—C10	35.2 (2)	C13—C12—C17—C18	−179.86 (16)
C8—C9—C10—N3	7.0 (2)	C11—C12—C17—C18	−2.6 (2)
C8—C9—C10—C11	−170.43 (14)	N3—C2—N1—C1	1.4 (2)
C9—C10—C11—O1	162.17 (16)	N2—C1—N1—C2	−1.1 (2)
N3—C10—C11—O1	−15.4 (2)	N1—C1—N2—N3	0.3 (2)
C9—C10—C11—C12	−16.3 (2)	N1—C2—N3—N2	−1.3 (2)
N3—C10—C11—C12	166.14 (13)	N1—C2—N3—C10	179.01 (15)
O1—C11—C12—C13	131.04 (18)	C1—N2—N3—C2	0.56 (18)
C10—C11—C12—C13	−50.6 (2)	C1—N2—N3—C10	−179.71 (13)
O1—C11—C12—C17	−46.2 (2)	C9—C10—N3—C2	−113.9 (2)
C10—C11—C12—C17	132.18 (16)	C11—C10—N3—C2	63.8 (2)
C17—C12—C13—C14	−0.4 (2)	C9—C10—N3—N2	66.43 (19)
C11—C12—C13—C14	−177.68 (15)	C11—C10—N3—N2	−115.87 (15)