(Z)-1,3-Bis(4-chloro­phen­yl)-2-(1H-1,2,4-triazol-1-yl)prop-2-en-1-one

Abstract

In the title mol­ecule, C₁₇H₁₁Cl₂N₃O, the C=C bond connecting the triazole and 4-chloro­phenyl groups adopts a Z geometry. The dihedral angles formed by the triazole ring and the 4-chloro substituted benzene rings are 67.3 (1) and 59.1 (1)°. The dihedral angle between the two benzene rings is 73.5 (1)°.

Related literature  

For the pharmacological activity of triazole compounds, see: Wang & Zhou (2011 ▶); Zhou & Wang (2012 ▶). For the biological activity of chalcones, see: Jin et al. (2010 ▶). For related structures, see: Wang et al. (2009 ▶); Yan et al. (2009 ▶). For the synthesis, see: Yin et al. (2012 ▶).

Experimental  

Crystal data  

• C₁₇H₁₁Cl₂N₃O

• M _r = 344.19

• Triclinic,

• a = 5.588 (3) Å

• b = 11.850 (7) Å

• c = 12.653 (8) Å

• α = 74.787 (10)°

• β = 88.884 (9)°

• γ = 86.461 (9)°

• V = 807.1 (8) ų

• Z = 2

• Mo Kα radiation

• μ = 0.41 mm⁻¹

• T = 296 K

• 0.22 × 0.18 × 0.15 mm

Data collection  

• Bruker APEXII CCD diffractometer

• Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.915, T _max = 0.941

• 4414 measured reflections

• 3104 independent reflections

• 2458 reflections with I > 2σ(I)

• R _int = 0.013

Refinement  

• R[F ² > 2σ(F ²)] = 0.037

• wR(F ²) = 0.105

• S = 1.02

• 3104 reflections

• 208 parameters

• H-atom parameters constrained

• Δρ_max = 0.21 e Å⁻³

• Δρ_min = −0.26 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Supplementary material file. DOI: 10.1107/S1600536812016170/lh5453Isup3.cml

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

supplementary crystallographic information

Comment

Triazoles as an important type of five-membered aromatic heterocycles have been paid increasing attention for their broad bioactive spectrum in medicinal chemistry (Wang et al., 2011; Zhou et al., 2012). The incorporation of a triazole ring into chalcone skeletons could largely improve bioactivities like antimicrobial, anticancer, antiviral and anti-inflammatory (Jin et al., 2010). In view of this, we have synthesized and reported some triazolylchalcones (Wang et al., 2009; Yan et al., 2009; Yin et al., 2012). Herein, the crystal structure of title compound (I) is reported.

The molecular structure of (I) is shown in Fig. 1. The C8═C11 bond adopts a Z geometry. The atoms in the region of the double bond have an essentially planar arrangement i.e. the r.m.s. deviation the atoms C7/C8/C11/C12/N1 is 0.025 Å. The torsion angles of C12–C11═C8–C7 and C12–C11═C8–N1 are -174.66 (17)° and 5.7 (3)°. The dihedral angles formed by the triazole ring and the 4-chloro-substituted benzene rings are 67.3 (1)° (C1-C6) and 59.1 (1)° (C12-C17), respectively. The dihedral angle between the two benzene rings is 73.5 (1)°.

Experimental

Compound (I) was prepared according to the procedure of Yin et al. (2012). Single crystals were grown by slow evaporation of a solution of (I) in ethyl acetate and petroleum ether (1:3, V/V) at room temperature.

Refinement

H atoms were placed at calculated position with C—H = 0.93 Å. The U_iso(H) values were set equal to 1.2U_eq(C).

Figures

Fig. 1.

The molecular structure of (I), showing the displacement ellipsoids at the 50% probability level.

Crystal data

C17H11Cl2N3O	Z = 2
Mr = 344.19	F(000) = 352
Triclinic, P1	Dx = 1.416 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.588 (3) Å	Cell parameters from 2086 reflections
b = 11.850 (7) Å	θ = 3.3–27.2°
c = 12.653 (8) Å	µ = 0.41 mm−1
α = 74.787 (10)°	T = 296 K
β = 88.884 (9)°	Block, yellow
γ = 86.461 (9)°	0.22 × 0.18 × 0.15 mm
V = 807.1 (8) Å3

Data collection

Bruker APEXII CCD diffractometer	3104 independent reflections
Radiation source: fine-focus sealed tube	2458 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.013
φ and ω scans	θmax = 26.0°, θmin = 3.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −6→6
Tmin = 0.915, Tmax = 0.941	k = −7→14
4414 measured reflections	l = −14→15

Refinement

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0515P)2 + 0.1439P] where P = (Fo2 + 2Fc2)/3
3104 reflections	(Δ/σ)max = 0.001
208 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.26 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
Cl1	1.58438 (14)	0.60011 (6)	−0.17465 (5)	0.1010 (3)
Cl2	0.14916 (9)	0.80981 (5)	0.64259 (4)	0.07445 (19)
C1	1.4458 (4)	0.6784 (2)	−0.08893 (15)	0.0703 (6)
C2	1.5551 (4)	0.7730 (2)	−0.07247 (16)	0.0719 (6)
H2A	1.6975	0.7964	−0.1085	0.086*
C3	1.4505 (4)	0.83280 (18)	−0.00168 (16)	0.0654 (5)
H3A	1.5235	0.8969	0.0100	0.079*
C4	1.2364 (3)	0.79806 (16)	0.05257 (14)	0.0532 (4)
C5	1.1286 (4)	0.70284 (18)	0.03344 (15)	0.0637 (5)
H5A	0.9861	0.6788	0.0691	0.076*
C6	1.2320 (4)	0.6435 (2)	−0.03847 (17)	0.0733 (6)
H6A	1.1579	0.5808	−0.0525	0.088*
C7	1.1296 (3)	0.87101 (16)	0.12331 (15)	0.0557 (4)
C8	0.9716 (3)	0.81969 (14)	0.21872 (14)	0.0487 (4)
C9	1.1937 (3)	0.63087 (16)	0.31196 (15)	0.0582 (5)
H9A	1.3439	0.6594	0.3154	0.070*
C10	0.9086 (4)	0.52367 (17)	0.32519 (19)	0.0736 (6)
H10A	0.8222	0.4566	0.3425	0.088*
C11	0.8102 (3)	0.88957 (15)	0.25517 (14)	0.0522 (4)
H11A	0.7981	0.9669	0.2131	0.063*
C12	0.6506 (3)	0.86366 (14)	0.35025 (13)	0.0475 (4)
C13	0.6915 (3)	0.77059 (16)	0.44322 (14)	0.0554 (4)
H13A	0.8248	0.7190	0.4452	0.067*
C14	0.5387 (3)	0.75364 (16)	0.53190 (15)	0.0564 (4)
H14A	0.5684	0.6911	0.5931	0.068*
C15	0.3405 (3)	0.83027 (15)	0.52953 (14)	0.0524 (4)
C16	0.2943 (3)	0.92271 (17)	0.43910 (16)	0.0637 (5)
H16A	0.1595	0.9733	0.4373	0.076*
C17	0.4495 (3)	0.93960 (15)	0.35136 (15)	0.0586 (5)
H17A	0.4198	1.0033	0.2911	0.070*
N1	0.9986 (2)	0.69650 (11)	0.26747 (11)	0.0466 (3)
N2	0.8100 (3)	0.62670 (13)	0.27539 (14)	0.0621 (4)
N3	1.1434 (3)	0.52092 (14)	0.34991 (15)	0.0737 (5)
O1	1.1701 (3)	0.97469 (12)	0.10500 (12)	0.0776 (4)

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
Cl1	0.1303 (6)	0.1091 (5)	0.0559 (3)	0.0454 (4)	0.0020 (3)	−0.0198 (3)
Cl2	0.0717 (3)	0.0773 (4)	0.0663 (3)	0.0119 (3)	0.0173 (2)	−0.0097 (3)
C1	0.0846 (14)	0.0750 (14)	0.0403 (10)	0.0208 (11)	0.0000 (9)	−0.0016 (9)
C2	0.0633 (12)	0.0815 (15)	0.0578 (12)	0.0082 (11)	0.0113 (9)	0.0014 (10)
C3	0.0629 (11)	0.0632 (12)	0.0620 (12)	−0.0054 (9)	0.0100 (9)	−0.0024 (9)
C4	0.0524 (10)	0.0568 (10)	0.0446 (9)	−0.0020 (8)	0.0029 (7)	−0.0033 (8)
C5	0.0644 (12)	0.0749 (13)	0.0514 (11)	−0.0129 (10)	0.0062 (9)	−0.0143 (9)
C6	0.0929 (16)	0.0733 (13)	0.0536 (11)	−0.0080 (11)	−0.0012 (11)	−0.0158 (10)
C7	0.0547 (10)	0.0540 (11)	0.0542 (10)	−0.0096 (8)	0.0019 (8)	−0.0052 (8)
C8	0.0478 (9)	0.0483 (9)	0.0477 (9)	−0.0061 (7)	−0.0004 (7)	−0.0079 (7)
C9	0.0458 (9)	0.0616 (11)	0.0635 (11)	0.0033 (8)	0.0018 (8)	−0.0117 (9)
C10	0.0772 (14)	0.0486 (11)	0.0915 (16)	−0.0111 (10)	0.0164 (12)	−0.0116 (10)
C11	0.0581 (10)	0.0459 (9)	0.0495 (9)	−0.0011 (8)	−0.0021 (8)	−0.0070 (7)
C12	0.0507 (9)	0.0439 (9)	0.0483 (9)	−0.0003 (7)	−0.0032 (7)	−0.0131 (7)
C13	0.0527 (10)	0.0569 (10)	0.0523 (10)	0.0133 (8)	−0.0012 (8)	−0.0102 (8)
C14	0.0606 (11)	0.0529 (10)	0.0495 (10)	0.0077 (8)	−0.0020 (8)	−0.0051 (8)
C15	0.0532 (10)	0.0534 (10)	0.0514 (10)	0.0010 (8)	0.0013 (8)	−0.0161 (8)
C16	0.0636 (11)	0.0584 (11)	0.0634 (12)	0.0193 (9)	0.0022 (9)	−0.0113 (9)
C17	0.0719 (12)	0.0465 (9)	0.0517 (10)	0.0112 (8)	−0.0022 (9)	−0.0061 (8)
N1	0.0400 (7)	0.0463 (7)	0.0520 (8)	−0.0052 (6)	0.0049 (6)	−0.0101 (6)
N2	0.0496 (8)	0.0545 (9)	0.0815 (11)	−0.0141 (7)	0.0071 (8)	−0.0146 (8)
N3	0.0744 (11)	0.0538 (10)	0.0842 (12)	0.0101 (8)	0.0069 (9)	−0.0065 (8)
O1	0.0930 (10)	0.0584 (9)	0.0789 (10)	−0.0199 (7)	0.0262 (8)	−0.0121 (7)

Geometric parameters (Å, º)

Cl1—C1	1.745 (2)	C9—N1	1.342 (2)
Cl2—C15	1.743 (2)	C9—H9A	0.9300
C1—C2	1.372 (3)	C10—N2	1.311 (3)
C1—C6	1.379 (3)	C10—N3	1.351 (3)
C2—C3	1.381 (3)	C10—H10A	0.9300
C2—H2A	0.9300	C11—C12	1.461 (2)
C3—C4	1.398 (3)	C11—H11A	0.9300
C3—H3A	0.9300	C12—C13	1.397 (2)
C4—C5	1.389 (3)	C12—C17	1.398 (2)
C4—C7	1.492 (3)	C13—C14	1.377 (2)
C5—C6	1.386 (3)	C13—H13A	0.9300
C5—H5A	0.9300	C14—C15	1.384 (2)
C6—H6A	0.9300	C14—H14A	0.9300
C7—O1	1.224 (2)	C15—C16	1.377 (3)
C7—C8	1.499 (2)	C16—C17	1.375 (3)
C8—C11	1.343 (2)	C16—H16A	0.9300
C8—N1	1.428 (2)	C17—H17A	0.9300
C9—N3	1.311 (3)	N1—N2	1.366 (2)
C2—C1—C6	121.6 (2)	N2—C10—H10A	122.1
C2—C1—Cl1	118.80 (18)	N3—C10—H10A	122.1
C6—C1—Cl1	119.6 (2)	C8—C11—C12	130.38 (16)
C1—C2—C3	119.1 (2)	C8—C11—H11A	114.8
C1—C2—H2A	120.5	C12—C11—H11A	114.8
C3—C2—H2A	120.5	C13—C12—C17	117.31 (16)
C2—C3—C4	120.7 (2)	C13—C12—C11	124.22 (15)
C2—C3—H3A	119.6	C17—C12—C11	118.39 (15)
C4—C3—H3A	119.6	C14—C13—C12	121.34 (16)
C5—C4—C3	118.93 (19)	C14—C13—H13A	119.3
C5—C4—C7	123.74 (16)	C12—C13—H13A	119.3
C3—C4—C7	117.23 (18)	C13—C14—C15	119.61 (16)
C6—C5—C4	120.40 (19)	C13—C14—H14A	120.2
C6—C5—H5A	119.8	C15—C14—H14A	120.2
C4—C5—H5A	119.8	C16—C15—C14	120.58 (17)
C1—C6—C5	119.2 (2)	C16—C15—Cl2	119.85 (14)
C1—C6—H6A	120.4	C14—C15—Cl2	119.56 (14)
C5—C6—H6A	120.4	C17—C16—C15	119.36 (17)
O1—C7—C4	120.59 (16)	C17—C16—H16A	120.3
O1—C7—C8	118.20 (17)	C15—C16—H16A	120.3
C4—C7—C8	121.21 (16)	C16—C17—C12	121.78 (17)
C11—C8—N1	122.27 (15)	C16—C17—H17A	119.1
C11—C8—C7	119.71 (16)	C12—C17—H17A	119.1
N1—C8—C7	118.02 (14)	C9—N1—N2	109.33 (15)
N3—C9—N1	110.62 (17)	C9—N1—C8	129.36 (14)
N3—C9—H9A	124.7	N2—N1—C8	121.31 (13)
N1—C9—H9A	124.7	C10—N2—N1	101.71 (16)
N2—C10—N3	115.89 (18)	C9—N3—C10	102.45 (16)
C6—C1—C2—C3	1.4 (3)	C17—C12—C13—C14	0.6 (3)
Cl1—C1—C2—C3	−177.75 (14)	C11—C12—C13—C14	177.44 (17)
C1—C2—C3—C4	0.0 (3)	C12—C13—C14—C15	−0.2 (3)
C2—C3—C4—C5	−0.6 (3)	C13—C14—C15—C16	0.4 (3)
C2—C3—C4—C7	−177.11 (17)	C13—C14—C15—Cl2	−179.19 (14)
C3—C4—C5—C6	−0.1 (3)	C14—C15—C16—C17	−1.1 (3)
C7—C4—C5—C6	176.17 (18)	Cl2—C15—C16—C17	178.52 (15)
C2—C1—C6—C5	−2.1 (3)	C15—C16—C17—C12	1.6 (3)
Cl1—C1—C6—C5	177.06 (15)	C13—C12—C17—C16	−1.3 (3)
C4—C5—C6—C1	1.4 (3)	C11—C12—C17—C16	−178.32 (18)
C5—C4—C7—O1	−150.2 (2)	N3—C9—N1—N2	−0.5 (2)
C3—C4—C7—O1	26.1 (3)	N3—C9—N1—C8	178.82 (17)
C5—C4—C7—C8	30.1 (3)	C11—C8—N1—C9	−122.4 (2)
C3—C4—C7—C8	−153.57 (17)	C7—C8—N1—C9	58.0 (2)
O1—C7—C8—C11	25.1 (3)	C11—C8—N1—N2	56.9 (2)
C4—C7—C8—C11	−155.23 (17)	C7—C8—N1—N2	−122.75 (17)
O1—C7—C8—N1	−155.21 (17)	N3—C10—N2—N1	0.0 (2)
C4—C7—C8—N1	24.5 (2)	C9—N1—N2—C10	0.3 (2)
N1—C8—C11—C12	5.7 (3)	C8—N1—N2—C10	−179.08 (16)
C7—C8—C11—C12	−174.66 (17)	N1—C9—N3—C10	0.5 (2)
C8—C11—C12—C13	23.4 (3)	N2—C10—N3—C9	−0.3 (3)
C8—C11—C12—C17	−159.82 (19)