1,5-Bis(2,6-dichloro­phen­yl)-3-[(1H-1,2,4-triazol-1-yl)meth­yl]penta-1,4-dien-3-ol

Xu, L.-Z.; Zhang, G.-S.; Yi, X.; An, G.-W.; Xu, Z.-J.

doi:10.1107/S1600536807058898

1,5-Bis(2,6-dichlorophenyl)-3-[(1H-1,2,4-triazol-1-yl)methyl]penta-1,4-dien-3-ol

L.-Z. Xu, G.-S. Zhang, X. Yi, G.-W. An and Z.-J. Xu

The title compound, C₂₀H₁₅Cl₄N₃O, was prepared by the reaction of 2,2-bis(2,6-dichlorostyryl)oxirane and 1,2,4-triazole. In the crystal structure, molecules assemble along the b axis, forming helical suprastructures, which further assemble along the c axis, forming two-dimensional layer structures.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807058898/hg2350sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807058898/hg2350Isup2.hkl Contains datablock I

CCDC reference: 673044

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Key indicators

Single-crystal X-ray study
T = 153 K
Mean (C-C)= 0.003 Å
R factor = 0.031
wR factor = 0.085
Data-to-parameter ratio = 13.4

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No errors found in this datablock

Comment top

Derivatives of 1,2,4-triazole are known to exhibit diverse applications in the fields of medicine, agriculture and industry. Among the agriculture profiles of various 1,2,4-triazole and its derivatives, their fungicidal, bactericidal, pesticidal and plant growth properties (Massa et al., 1992) seem to be the most widely documented. For these reasons, the structures of substituted 1,2,4-triazole have been a subject of interest in our laboratory. The crystal structure of the title compound is presented here.

The bond lengths and angles are normal for this type of compound (Rong et al., 2006). The dihedral angles formed by phenyl ring (C1 - C6) and phenyl ring (C13 –C18) with plane (N1/N2/N3/C19/C20) are 34.20 (2) and 10.10 (2)°, respectively. The dihedral angle between the benzene rings is 24.41 (3)°. The molecules assemble to form helical superstructures along the b axis. The helic pitch is 10.65 (2) Å. The right-handed and left-handed helix associate through weak hydrogen bonds, which further assemble along c axis to form two-dimensional layer structure through O—H···N hydrogen bonds.

Related literature top

For related literature, see: Graham & Jorg (1985); Massa et al. (1992); Rong et al. (2006).

Experimental top

A mixture of 1,2,4-triazole 0.90 g (0.013 mol), 2,2-bis(2,6-dichlorostyryl)oxirane 3.86 g (0.01 mol) dissolved in DMF and powdered potassium carbonate 0.1 g was stirred vigorously at gentle reflux for 2 h (Graham et al., 1985). The reaction mixture was cooled, then concentrated by removing the solvent under reduced pressure·The residue was taken up in water. The solid residue was then recrystallized from ethanol to give 3-((1H-1,2,4-triazol-1-yl)methyl)-1,5-bis(2,6-dichlorophenyl) penta-1,4-dien-3-ol 3.64 g(yield 80%). Single crystals suitable for X-ray measurement were obtained by recrystallization from methanol at room temperature.

Computing details top

Data collection: RAPID-AUTO (Rigaku 2004); cell refinement: RAPID-AUTO (Rigaku 2004); data reduction: RAPID-AUTO (Rigaku 2004); program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL (Sheldrick, 2001; molecular graphics: SHELXTL (Sheldrick, 2001; software used to prepare material for publication: SHELXTL (Sheldrick, 2001.

Figures top

	Fig. 1. View of the title compound (I), with displacement ellipsoids drawn at the 35% probability level.
	Fig. 2. A packing diagram of the molecule of the title compound, view down b axis. Hydrogen bonds are shown as dashed lines.

1,5-Bis(2,6-dichlorophenyl)-3-[(1H-1,2,4-triazol-1-yl)methyl]penta-1,4-dien-3-ol top

Crystal data top

C₂₀H₁₅Cl₄N₃O	F(000) = 928
M_r = 455.15	D_x = 1.535 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1494 reflections
a = 8.3413 (17) Å	θ = 2.6–26.4°
b = 10.652 (2) Å	µ = 0.62 mm⁻¹
c = 22.229 (4) Å	T = 153 K
β = 94.32 (3)°	Block, colorless
V = 1969.5 (7) Å³	0.32 × 0.22 × 0.16 mm
Z = 4

Data collection top

Rigaku RAXIS RAPID IP area-detector diffractometer	3470 independent reflections
Radiation source: Rotating Anode	2901 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ω Oscillation scans	θ_max = 25.0°, θ_min = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi 1995)	h = −9→9
T_min = 0.827, T_max = 0.908	k = −12→11
15134 measured reflections	l = −26→26

Refinement top

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)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.085	w = 1/[σ²(F_o²) + (0.0359P)² + 0.8502P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
3470 reflections	Δρ_max = 0.27 e Å⁻³
258 parameters	Δρ_min = −0.22 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0048 (6)

Crystal data top

C₂₀H₁₅Cl₄N₃O	V = 1969.5 (7) Å³
M_r = 455.15	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.3413 (17) Å	µ = 0.62 mm⁻¹
b = 10.652 (2) Å	T = 153 K
c = 22.229 (4) Å	0.32 × 0.22 × 0.16 mm
β = 94.32 (3)°

Data collection top

Rigaku RAXIS RAPID IP area-detector diffractometer	3470 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi 1995)	2901 reflections with I > 2σ(I)
T_min = 0.827, T_max = 0.908	R_int = 0.031
15134 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.27 e Å⁻³
3470 reflections	Δρ_min = −0.22 e Å⁻³
258 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
Cl4	0.43666 (7)	0.42402 (6)	0.34867 (3)	0.06239 (19)
Cl2	0.33568 (7)	0.22308 (5)	0.23550 (3)	0.05817 (18)
Cl3	0.85225 (8)	0.35813 (5)	0.54500 (3)	0.0637 (2)
Cl1	0.23987 (7)	−0.25254 (6)	0.31663 (3)	0.0666 (2)
O1	0.64236 (17)	−0.00926 (13)	0.42224 (7)	0.0441 (4)
N1	0.98450 (18)	0.03373 (14)	0.38889 (7)	0.0387 (4)
C13	0.2879 (2)	−0.01739 (17)	0.27484 (8)	0.0351 (4)
C6	0.6561 (2)	0.39721 (17)	0.44453 (8)	0.0348 (4)
N2	1.0809 (2)	0.13526 (15)	0.38301 (8)	0.0473 (4)
C10	0.8402 (2)	0.01560 (19)	0.34845 (9)	0.0433 (5)
H10A	0.8277	−0.0752	0.3397	0.052*
H10B	0.8554	0.0587	0.3098	0.052*
C9	0.6840 (2)	0.06435 (16)	0.37317 (8)	0.0348 (4)
C11	0.5554 (2)	0.05100 (18)	0.32121 (8)	0.0384 (4)
H11A	0.5765	0.0882	0.2838	0.046*
C15	0.0685 (2)	−0.1425 (2)	0.22533 (9)	0.0471 (5)
H15A	0.0088	−0.2185	0.2234	0.057*
N3	1.1824 (2)	0.00913 (18)	0.45797 (8)	0.0521 (5)
C12	0.4179 (2)	−0.00754 (18)	0.32389 (8)	0.0383 (4)
H12A	0.3998	−0.0477	0.3609	0.046*
C8	0.6932 (2)	0.20331 (16)	0.38717 (8)	0.0352 (4)
H8A	0.7318	0.2559	0.3569	0.042*
C14	0.1950 (2)	−0.12640 (19)	0.26875 (8)	0.0400 (4)
C4	0.7604 (3)	0.58210 (19)	0.50010 (9)	0.0500 (5)
H4A	0.8260	0.6162	0.5329	0.060*
C1	0.5691 (2)	0.48093 (18)	0.40644 (9)	0.0414 (4)
C5	0.7486 (2)	0.45377 (18)	0.49228 (8)	0.0397 (4)
C17	0.1171 (2)	0.0629 (2)	0.18888 (9)	0.0495 (5)
H17A	0.0916	0.1289	0.1610	0.059*
C20	1.1960 (2)	0.1150 (2)	0.42536 (9)	0.0475 (5)
H20A	1.2836	0.1714	0.4327	0.057*
C18	0.2413 (2)	0.07738 (18)	0.23329 (9)	0.0404 (4)
C7	0.6534 (2)	0.25908 (17)	0.43680 (8)	0.0367 (4)
H7A	0.6215	0.2085	0.4690	0.044*
C19	1.0475 (2)	−0.0394 (2)	0.43300 (9)	0.0477 (5)
H19A	1.0018	−0.1163	0.4450	0.057*
C2	0.5793 (3)	0.60988 (19)	0.41337 (9)	0.0473 (5)
H2B	0.5191	0.6636	0.3860	0.057*
C16	0.0304 (2)	−0.0475 (2)	0.18522 (9)	0.0525 (6)
H16A	−0.0554	−0.0576	0.1550	0.063*
C3	0.6762 (3)	0.65986 (19)	0.45980 (10)	0.0508 (5)
H3B	0.6852	0.7484	0.4641	0.061*
H1A	0.686 (3)	0.006 (2)	0.4516 (11)	0.050 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl4	0.0641 (4)	0.0592 (3)	0.0593 (3)	0.0088 (3)	−0.0255 (3)	−0.0059 (3)
Cl2	0.0587 (3)	0.0427 (3)	0.0695 (4)	0.0006 (2)	−0.0191 (3)	0.0066 (2)
Cl3	0.0799 (4)	0.0533 (3)	0.0535 (3)	0.0072 (3)	−0.0249 (3)	0.0025 (3)
Cl1	0.0618 (4)	0.0589 (4)	0.0756 (4)	−0.0161 (3)	−0.0185 (3)	0.0215 (3)
O1	0.0496 (8)	0.0393 (7)	0.0408 (8)	−0.0077 (6)	−0.0145 (7)	0.0034 (6)
N1	0.0343 (8)	0.0369 (8)	0.0433 (9)	0.0072 (7)	−0.0084 (7)	−0.0077 (7)
C13	0.0291 (9)	0.0435 (10)	0.0321 (9)	0.0039 (8)	−0.0022 (7)	−0.0061 (8)
C6	0.0360 (9)	0.0345 (9)	0.0342 (9)	0.0006 (8)	0.0053 (8)	−0.0016 (8)
N2	0.0450 (9)	0.0413 (9)	0.0542 (10)	0.0001 (8)	−0.0055 (8)	−0.0035 (8)
C10	0.0387 (10)	0.0443 (11)	0.0445 (11)	0.0073 (8)	−0.0133 (9)	−0.0144 (9)
C9	0.0341 (9)	0.0330 (9)	0.0355 (9)	0.0016 (7)	−0.0090 (8)	−0.0011 (7)
C11	0.0366 (10)	0.0428 (10)	0.0345 (10)	0.0046 (8)	−0.0067 (8)	−0.0006 (8)
C15	0.0343 (10)	0.0568 (13)	0.0492 (12)	−0.0051 (9)	−0.0040 (9)	−0.0114 (10)
N3	0.0391 (9)	0.0672 (12)	0.0482 (10)	0.0071 (8)	−0.0092 (8)	−0.0006 (9)
C12	0.0386 (10)	0.0405 (10)	0.0344 (10)	0.0043 (8)	−0.0062 (8)	−0.0037 (8)
C8	0.0326 (9)	0.0339 (9)	0.0385 (10)	0.0019 (8)	−0.0004 (8)	0.0014 (8)
C14	0.0334 (9)	0.0475 (11)	0.0385 (10)	0.0024 (8)	−0.0015 (8)	−0.0016 (8)
C4	0.0618 (13)	0.0412 (11)	0.0460 (12)	−0.0055 (10)	−0.0027 (10)	−0.0079 (9)
C1	0.0428 (10)	0.0421 (11)	0.0385 (10)	0.0021 (8)	−0.0013 (8)	−0.0025 (8)
C5	0.0427 (10)	0.0385 (10)	0.0372 (10)	0.0022 (8)	−0.0009 (8)	0.0023 (8)
C17	0.0425 (11)	0.0588 (13)	0.0447 (11)	0.0090 (10)	−0.0127 (9)	0.0024 (10)
C20	0.0379 (10)	0.0524 (12)	0.0513 (12)	−0.0012 (9)	−0.0039 (9)	−0.0129 (10)
C18	0.0358 (10)	0.0420 (10)	0.0422 (10)	0.0034 (8)	−0.0050 (8)	−0.0037 (9)
C7	0.0371 (9)	0.0347 (9)	0.0378 (10)	0.0002 (8)	−0.0003 (8)	0.0016 (8)
C19	0.0417 (11)	0.0462 (11)	0.0536 (12)	0.0072 (9)	−0.0062 (10)	0.0034 (10)
C2	0.0556 (12)	0.0396 (11)	0.0464 (11)	0.0093 (9)	0.0027 (10)	0.0066 (9)
C16	0.0374 (11)	0.0726 (15)	0.0447 (12)	0.0037 (10)	−0.0147 (9)	−0.0085 (11)
C3	0.0669 (14)	0.0325 (10)	0.0535 (13)	−0.0003 (10)	0.0083 (11)	−0.0021 (9)

Geometric parameters (Å, º) top

Cl4—C1	1.739 (2)	C15—C16	1.370 (3)
Cl2—C18	1.739 (2)	C15—C14	1.386 (3)
Cl3—C5	1.7341 (19)	C15—H15A	0.9500
Cl1—C14	1.737 (2)	N3—C19	1.322 (3)
O1—C9	1.408 (2)	N3—C20	1.350 (3)
O1—H1A	0.74 (2)	C12—H12A	0.9500
N1—C19	1.329 (2)	C8—C7	1.317 (3)
N1—N2	1.360 (2)	C8—H8A	0.9500
N1—C10	1.460 (2)	C4—C3	1.374 (3)
C13—C14	1.397 (3)	C4—C5	1.381 (3)
C13—C18	1.403 (3)	C4—H4A	0.9500
C13—C12	1.483 (2)	C1—C2	1.384 (3)
C6—C1	1.395 (3)	C17—C16	1.380 (3)
C6—C5	1.400 (3)	C17—C18	1.385 (3)
C6—C7	1.481 (2)	C17—H17A	0.9500
N2—C20	1.311 (3)	C20—H20A	0.9500
C10—C9	1.542 (3)	C7—H7A	0.9500
C10—H10A	0.9900	C19—H19A	0.9500
C10—H10B	0.9900	C2—C3	1.370 (3)
C9—C8	1.513 (2)	C2—H2B	0.9500
C9—C11	1.523 (2)	C16—H16A	0.9500
C11—C12	1.310 (3)	C3—H3B	0.9500
C11—H11A	0.9500

C9—O1—H1A	115.4 (19)	C15—C14—C13	123.92 (18)
C19—N1—N2	109.47 (15)	C15—C14—Cl1	116.65 (16)
C19—N1—C10	129.67 (17)	C13—C14—Cl1	119.42 (14)
N2—N1—C10	120.81 (16)	C3—C4—C5	119.11 (19)
C14—C13—C18	114.21 (16)	C3—C4—H4A	120.4
C14—C13—C12	119.99 (16)	C5—C4—H4A	120.4
C18—C13—C12	125.74 (17)	C2—C1—C6	122.84 (18)
C1—C6—C5	114.62 (17)	C2—C1—Cl4	117.28 (15)
C1—C6—C7	124.18 (16)	C6—C1—Cl4	119.86 (15)
C5—C6—C7	121.20 (16)	C4—C5—C6	123.48 (18)
C20—N2—N1	101.93 (16)	C4—C5—Cl3	117.98 (15)
N1—C10—C9	114.57 (15)	C6—C5—Cl3	118.53 (15)
N1—C10—H10A	108.6	C16—C17—C18	119.83 (19)
C9—C10—H10A	108.6	C16—C17—H17A	120.1
N1—C10—H10B	108.6	C18—C17—H17A	120.1
C9—C10—H10B	108.6	N2—C20—N3	115.85 (18)
H10A—C10—H10B	107.6	N2—C20—H20A	122.1
O1—C9—C8	113.39 (15)	N3—C20—H20A	122.1
O1—C9—C11	109.57 (15)	C17—C18—C13	122.98 (18)
C8—C9—C11	105.62 (14)	C17—C18—Cl2	115.59 (15)
O1—C9—C10	110.66 (15)	C13—C18—Cl2	121.41 (14)
C8—C9—C10	111.81 (15)	C8—C7—C6	122.85 (17)
C11—C9—C10	105.33 (15)	C8—C7—H7A	118.6
C12—C11—C9	125.37 (18)	C6—C7—H7A	118.6
C12—C11—H11A	117.3	N3—C19—N1	110.91 (19)
C9—C11—H11A	117.3	N3—C19—H19A	124.5
C16—C15—C14	119.26 (19)	N1—C19—H19A	124.5
C16—C15—H15A	120.4	C3—C2—C1	119.81 (19)
C14—C15—H15A	120.4	C3—C2—H2B	120.1
C19—N3—C20	101.83 (17)	C1—C2—H2B	120.1
C11—C12—C13	126.46 (18)	C15—C16—C17	119.77 (17)
C11—C12—H12A	116.8	C15—C16—H16A	120.1
C13—C12—H12A	116.8	C17—C16—H16A	120.1
C7—C8—C9	126.96 (17)	C2—C3—C4	120.05 (19)
C7—C8—H8A	116.5	C2—C3—H3B	120.0
C9—C8—H8A	116.5	C4—C3—H3B	120.0

C19—N1—N2—C20	−0.5 (2)	C3—C4—C5—C6	0.9 (3)
C10—N1—N2—C20	−178.22 (16)	C3—C4—C5—Cl3	−178.38 (17)
C19—N1—C10—C9	87.3 (2)	C1—C6—C5—C4	−3.0 (3)
N2—N1—C10—C9	−95.5 (2)	C7—C6—C5—C4	177.26 (19)
N1—C10—C9—O1	−68.6 (2)	C1—C6—C5—Cl3	176.25 (14)
N1—C10—C9—C8	58.8 (2)	C7—C6—C5—Cl3	−3.5 (3)
N1—C10—C9—C11	173.04 (16)	N1—N2—C20—N3	0.1 (2)
O1—C9—C11—C12	7.5 (3)	C19—N3—C20—N2	0.3 (2)
C8—C9—C11—C12	−115.0 (2)	C16—C17—C18—C13	1.7 (3)
C10—C9—C11—C12	126.6 (2)	C16—C17—C18—Cl2	−177.19 (17)
C9—C11—C12—C13	177.26 (17)	C14—C13—C18—C17	−1.8 (3)
C14—C13—C12—C11	145.6 (2)	C12—C13—C18—C17	−179.10 (19)
C18—C13—C12—C11	−37.2 (3)	C14—C13—C18—Cl2	177.03 (14)
O1—C9—C8—C7	−6.4 (2)	C12—C13—C18—Cl2	−0.2 (3)
C11—C9—C8—C7	113.6 (2)	C9—C8—C7—C6	−175.63 (16)
C10—C9—C8—C7	−132.37 (19)	C1—C6—C7—C8	57.6 (3)
C16—C15—C14—C13	0.4 (3)	C5—C6—C7—C8	−122.7 (2)
C16—C15—C14—Cl1	−178.21 (16)	C20—N3—C19—N1	−0.7 (2)
C18—C13—C14—C15	0.8 (3)	N2—N1—C19—N3	0.8 (2)
C12—C13—C14—C15	178.21 (18)	C10—N1—C19—N3	178.20 (18)
C18—C13—C14—Cl1	179.34 (14)	C6—C1—C2—C3	−1.0 (3)
C12—C13—C14—Cl1	−3.2 (2)	Cl4—C1—C2—C3	177.09 (17)
C5—C6—C1—C2	3.0 (3)	C14—C15—C16—C17	−0.6 (3)
C7—C6—C1—C2	−177.25 (19)	C18—C17—C16—C15	−0.4 (3)
C5—C6—C1—Cl4	−174.96 (14)	C1—C2—C3—C4	−1.4 (3)
C7—C6—C1—Cl4	4.7 (3)	C5—C4—C3—C2	1.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N3ⁱ	0.74 (2)	2.22 (2)	2.940 (2)	163 (2)

Symmetry code: (i) −x+2, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₅Cl₄N₃O
M_r	455.15
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	153
a, b, c (Å)	8.3413 (17), 10.652 (2), 22.229 (4)
β (°)	94.32 (3)
V (Å³)	1969.5 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.62
Crystal size (mm)	0.32 × 0.22 × 0.16

Data collection
Diffractometer	Rigaku RAXIS RAPID IP area-detector diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi 1995)
T_min, T_max	0.827, 0.908
No. of measured, independent and observed [I > 2σ(I)] reflections	15134, 3470, 2901
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.085, 1.06
No. of reflections	3470
No. of parameters	258
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.22

Computer programs: RAPID-AUTO (Rigaku 2004), SHELXTL (Sheldrick, 2001), SHELXTL (Sheldrick, 2001.