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

Dai, L.-L.; Yin, B.-T.; Lv, J.-S.; Cui, S.-F.; Zhou, C.-H.

doi:10.1107/S1600536812016170

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1456

doi:10.1107/S1600536812016170

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

Ling-Ling Dai,^a Ben-Tao Yin,^a Jing-Song Lv,^a Sheng-Feng Cui ^a and Cheng-He Zhou ^a ^*

^aLaboratory of Bioorganic & Medicinal Chemistry, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, People's Republic of China
^*Correspondence e-mail: zhouch@swu.edu.cn

(Received 8 April 2012; accepted 13 April 2012; online 21 April 2012)

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, $[P \overline 1]$
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) Å³
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[F² > 2σ(F²)] = 0.037
wR(F²) = 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812016170/lh5453sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812016170/lh5453Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812016170/lh5453Isup3.cml

checkCIF report

Comment top

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)°.

Related literature top

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 top

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.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I), showing the displacement ellipsoids at the 50% probability level.

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

Crystal data top

C₁₇H₁₁Cl₂N₃O	Z = 2
M_r = 344.19	F(000) = 352
Triclinic, P1	D_x = 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 top

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

Refinement top

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(F_o²) + (0.0515P)² + 0.1439P] where P = (F_o² + 2F_c²)/3
3104 reflections	(Δ/σ)_max = 0.001
208 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₇H₁₁Cl₂N₃O	γ = 86.461 (9)°
M_r = 344.19	V = 807.1 (8) Å³
Triclinic, P1	Z = 2
a = 5.588 (3) Å	Mo Kα radiation
b = 11.850 (7) Å	µ = 0.41 mm⁻¹
c = 12.653 (8) Å	T = 296 K
α = 74.787 (10)°	0.22 × 0.18 × 0.15 mm
β = 88.884 (9)°

Data collection top

Bruker APEXII CCD diffractometer	3104 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2458 reflections with I > 2σ(I)
T_min = 0.915, T_max = 0.941	R_int = 0.013
4414 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.105	H-atom parameters constrained
S = 1.02	Δρ_max = 0.21 e Å⁻³
3104 reflections	Δρ_min = −0.26 e Å⁻³
208 parameters

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

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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) top

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)

Experimental details

Crystal data
Chemical formula	C₁₇H₁₁Cl₂N₃O
M_r	344.19
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	5.588 (3), 11.850 (7), 12.653 (8)
α, β, γ (°)	74.787 (10), 88.884 (9), 86.461 (9)
V (Å³)	807.1 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.41
Crystal size (mm)	0.22 × 0.18 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.915, 0.941
No. of measured, independent and observed [I > 2σ(I)] reflections	4414, 3104, 2458
R_int	0.013
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.105, 1.02
No. of reflections	3104
No. of parameters	208
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.26

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was partially supported by the National Natural Science Foundation of China (No. 21172181), the Key Program of the Natural Science Foundation of Chongqing (CSTC2012jjB10026), the Specialized Research Fund for the Doctoral Program of Higher Education of China (SRFDP 20110182110007) and the Research Funds for the Central Universities (XDJK2011D007, XDJK2012B026).

References

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