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Acta Crystallogr Sect E Struct Rep Online. 2008 February 1; 64(Pt 2): o491.
Published online 2008 January 23. doi:  10.1107/S1600536808001505
PMCID: PMC2960291

2,2′-[1-(2,4,6-Trichlorophenyl)-1H-1,2,4-triazole-3,5-diyl]diphenol

Abstract

The title compound, C20H12Cl3N3O2, was synthesized by the reaction of 2-(2-hydroxy­phen­yl)benz[e][1,3]oxazin-4-one with 2,4,6-trichloro­phenyl­hydrazine in ethanol. The trichloro­phenyl ring is nearly perpendicular to the triazole plane [dihedral angle 80.56 (8)°], whereas the two hydroxy­phenyl rings are approximately coplanar with the triazole ring [dihedral angles of 2.79 (12) and 8.00 (14)°]. Intra­molecular O—H(...)N hydrogen bonding is observed between the hydroxy­phenyl and triazole rings.

Related literature

For general background, see: Nisbet-Brown et al. (2003 [triangle]); Steinhauser et al. (2004 [triangle]).

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Object name is e-64-0o491-scheme1.jpg

Experimental

Crystal data

  • C20H12Cl3N3O2
  • M r = 432.68
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o491-efi1.jpg
  • a = 14.328 (3) Å
  • b = 12.021 (2) Å
  • c = 12.014 (2) Å
  • β = 104.99 (3)°
  • V = 1998.7 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.48 mm−1
  • T = 293 (2) K
  • 0.20 × 0.20 × 0.18 mm

Data collection

  • Rigaku SCXmini diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 [triangle]) T min = 0.907, T max = 0.915
  • 16254 measured reflections
  • 3501 independent reflections
  • 3052 reflections with I > 2σ(I)
  • R int = 0.047

Refinement

  • R[F 2 > 2σ(F 2)] = 0.044
  • wR(F 2) = 0.104
  • S = 1.11
  • 3501 reflections
  • 261 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.35 e Å−3
  • Δρmin = −0.35 e Å−3

Data collection: CrystalClear (Rigaku, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL/PC (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL/PC; molecular graphics: SHELXTL/PC; software used to prepare material for publication: SHELXTL/PC.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808001505/xu2398sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808001505/xu2398Isup2.hkl

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

supplementary crystallographic information

Comment

3,5-Bis(2-hydroxyphenyl)-1-phenyl-1,2,4-triazole core has been successfully used a motif for the development of biologically interesting molecules, including active iron chelator (Nisbet-Brown et al., 2003; Steinhauser et al., 2004). We report here the crystal structure of the title triazole compound.

In the title molecule (Fig. 1), 3-(2-hydroxyphenyl) is almost co-planar with 1,2,4-triazole ring, dihedral angle being 2.79 (12)°. The 5-(2-hydroxyphenyl) ring forms a dihedral angle of 9.70 (13)° with triazole plane. The trichlorophenyl is nearly perpendicular to the triazole plane with a dihedral angle of 80.56 (8)°. Intra-molecular N—H···O hydrogen bonding is observed between hydroxyphenyl and triazole rings (Table 1).

Experimental

2-(2-Hydroxyphenyl)benz[e][1,3]oxazin-4-one (2.4 g) was mixed with 2,4,6-trichlorophenylhydrazine (2.2 g) in ethanol (30 ml). The mixture was refluxed for 3 h, after cooling to room temperature, the mixture was poured onto water and extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated on a rotary evaporator. The title compound was crystallized from methanol. The colourless crystals were obtained by slow evaporation of methanol.

Refinement

H atoms bound to carbon were placed in calculated positions and refined in riding mode with C—H = 0.93 Å and Uiso(H)=1.2Ueq(C). Hydroxyl H atoms were located in a difference Fourier map and refined isotropically.

Figures

Fig. 1.
The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

Crystal data

C20H12Cl3N3O2F(000) = 880
Mr = 432.68Dx = 1.438 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5847 reflections
a = 14.328 (3) Åθ = 3.0–28.4°
b = 12.021 (2) ŵ = 0.48 mm1
c = 12.014 (2) ÅT = 293 K
β = 104.99 (3)°Block, colourless
V = 1998.7 (7) Å30.20 × 0.20 × 0.18 mm
Z = 4

Data collection

Rigaku SCXmini diffractometer3501 independent reflections
Radiation source: fine-focus sealed tube3052 reflections with I > 2σ(I)
graphiteRint = 0.047
Detector resolution: 8.192 pixels mm-1θmax = 25.0°, θmin = 3.1°
ω scansh = −17→17
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)k = −14→14
Tmin = 0.907, Tmax = 0.915l = −14→14
16254 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H atoms treated by a mixture of independent and constrained refinement
S = 1.11w = 1/[σ2(Fo2) + (0.034P)2 + 0.892P] where P = (Fo2 + 2Fc2)/3
3501 reflections(Δ/σ)max < 0.001
261 parametersΔρmax = 0.36 e Å3
0 restraintsΔρmin = −0.35 e Å3

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 (Å2)

xyzUiso*/Ueq
Cl10.25005 (6)−0.25222 (6)0.53114 (7)0.0819 (3)
Cl20.36388 (5)0.15110 (5)0.40863 (6)0.0679 (2)
Cl30.49510 (6)−0.22786 (7)0.25494 (7)0.0814 (2)
N10.25668 (12)−0.00229 (15)0.52989 (14)0.0448 (4)
N20.29844 (12)0.00432 (15)0.64746 (14)0.0452 (4)
N30.14978 (11)0.08336 (15)0.60312 (14)0.0437 (4)
C10.33274 (16)0.04839 (17)0.89318 (18)0.0460 (5)
C20.34437 (19)0.0687 (2)1.0104 (2)0.0625 (6)
H2C0.40180.04901.06320.075*
C30.2707 (2)0.1181 (2)1.0485 (2)0.0678 (7)
H3B0.27880.13051.12680.081*
C40.1850 (2)0.1491 (2)0.9706 (2)0.0638 (7)
H4A0.13600.18230.99670.077*
C50.17289 (17)0.13019 (19)0.8534 (2)0.0531 (6)
H5A0.11550.15130.80140.064*
C60.24623 (14)0.07958 (17)0.81220 (17)0.0410 (5)
C70.23151 (14)0.05618 (16)0.68776 (17)0.0399 (4)
C80.16669 (14)0.04599 (17)0.50442 (18)0.0422 (5)
C90.09851 (15)0.06060 (19)0.38957 (18)0.0483 (5)
C100.01411 (16)0.1254 (2)0.3802 (2)0.0555 (6)
C11−0.04752 (19)0.1462 (2)0.2709 (3)0.0749 (8)
H11A−0.10240.18950.26450.090*
C12−0.0282 (2)0.1036 (3)0.1730 (3)0.0841 (9)
H12A−0.06910.12020.10120.101*
C130.0522 (2)0.0357 (3)0.1803 (2)0.0850 (9)
H13A0.06370.00450.11420.102*
C140.11476 (18)0.0154 (3)0.2880 (2)0.0698 (7)
H14A0.1687−0.02920.29300.084*
C150.31228 (14)−0.05594 (18)0.46145 (17)0.0430 (5)
C160.36702 (15)0.00659 (18)0.40185 (17)0.0454 (5)
C170.42321 (16)−0.0452 (2)0.33763 (19)0.0524 (6)
H17A0.4587−0.00350.29780.063*
C180.42469 (17)−0.1615 (2)0.3349 (2)0.0550 (6)
C190.37295 (18)−0.2260 (2)0.3944 (2)0.0609 (6)
H19A0.3758−0.30330.39230.073*
C200.31687 (16)−0.1727 (2)0.4570 (2)0.0520 (5)
O1−0.01130 (13)0.16967 (17)0.47345 (18)0.0718 (5)
H1A0.032 (2)0.156 (3)0.533 (3)0.087 (10)*
O20.40802 (12)−0.00300 (15)0.86177 (16)0.0593 (4)
H2A0.3949 (19)−0.013 (2)0.793 (2)0.064 (9)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0879 (5)0.0692 (5)0.1039 (6)−0.0208 (4)0.0528 (5)−0.0016 (4)
Cl20.0863 (5)0.0487 (3)0.0809 (5)0.0037 (3)0.0437 (4)0.0037 (3)
Cl30.0916 (5)0.0814 (5)0.0878 (5)0.0185 (4)0.0529 (4)−0.0117 (4)
N10.0394 (9)0.0578 (11)0.0380 (9)0.0044 (8)0.0116 (7)−0.0019 (8)
N20.0411 (9)0.0563 (11)0.0381 (9)0.0046 (8)0.0100 (7)−0.0020 (8)
N30.0368 (9)0.0510 (10)0.0449 (10)0.0025 (7)0.0136 (8)0.0033 (8)
C10.0516 (12)0.0416 (11)0.0455 (12)0.0003 (9)0.0140 (10)0.0031 (9)
C20.0686 (16)0.0713 (16)0.0440 (13)0.0056 (13)0.0083 (11)0.0029 (11)
C30.091 (2)0.0722 (17)0.0421 (14)0.0006 (15)0.0210 (13)−0.0036 (12)
C40.0784 (17)0.0642 (16)0.0581 (16)0.0057 (13)0.0345 (14)−0.0086 (12)
C50.0543 (13)0.0559 (14)0.0511 (13)0.0070 (11)0.0176 (11)−0.0018 (10)
C60.0460 (11)0.0383 (10)0.0411 (11)−0.0023 (9)0.0152 (9)0.0008 (8)
C70.0383 (10)0.0419 (11)0.0409 (11)−0.0005 (8)0.0130 (9)0.0016 (8)
C80.0358 (10)0.0487 (12)0.0438 (12)−0.0022 (9)0.0136 (9)0.0033 (9)
C90.0389 (11)0.0603 (14)0.0441 (12)−0.0057 (10)0.0079 (9)0.0071 (10)
C100.0417 (12)0.0601 (14)0.0614 (15)−0.0054 (10)0.0075 (11)0.0078 (11)
C110.0527 (15)0.0833 (19)0.075 (2)0.0037 (14)−0.0075 (14)0.0187 (15)
C120.0689 (19)0.114 (3)0.0552 (17)−0.0103 (17)−0.0095 (14)0.0228 (16)
C130.0680 (18)0.136 (3)0.0463 (16)−0.0049 (18)0.0067 (13)−0.0005 (16)
C140.0504 (14)0.110 (2)0.0458 (14)0.0045 (14)0.0061 (11)−0.0033 (14)
C150.0380 (10)0.0542 (13)0.0371 (11)0.0028 (9)0.0102 (9)−0.0043 (9)
C160.0453 (12)0.0498 (12)0.0418 (11)0.0031 (9)0.0124 (9)0.0005 (9)
C170.0521 (13)0.0618 (15)0.0476 (13)0.0048 (11)0.0210 (10)0.0042 (10)
C180.0550 (13)0.0635 (15)0.0506 (13)0.0096 (11)0.0210 (11)−0.0079 (11)
C190.0673 (16)0.0496 (13)0.0704 (17)0.0009 (11)0.0262 (13)−0.0083 (11)
C200.0499 (12)0.0550 (14)0.0537 (13)−0.0060 (10)0.0180 (10)−0.0029 (10)
O10.0472 (10)0.0926 (14)0.0714 (13)0.0185 (9)0.0078 (9)−0.0004 (10)
O20.0530 (10)0.0742 (12)0.0491 (10)0.0160 (8)0.0103 (8)0.0052 (9)

Geometric parameters (Å, °)

Cl1—C201.751 (2)C9—C141.410 (3)
Cl2—C161.740 (2)C9—C101.419 (3)
Cl3—C181.754 (2)C10—O11.371 (3)
N1—C81.374 (3)C10—C111.402 (4)
N1—N21.386 (2)C11—C121.375 (4)
N1—C151.437 (2)C11—H11A0.9300
N2—C71.335 (3)C12—C131.395 (4)
N3—C81.347 (3)C12—H12A0.9300
N3—C71.377 (3)C13—C141.392 (4)
C1—O21.378 (3)C13—H13A0.9300
C1—C21.396 (3)C14—H14A0.9300
C1—C61.414 (3)C15—C201.406 (3)
C2—C31.388 (4)C15—C161.408 (3)
C2—H2C0.9300C16—C171.397 (3)
C3—C41.387 (4)C17—C181.399 (3)
C3—H3B0.9300C17—H17A0.9300
C4—C51.393 (3)C18—C191.391 (3)
C4—H4A0.9300C19—C201.391 (3)
C5—C61.410 (3)C19—H19A0.9300
C5—H5A0.9300O1—H1A0.83 (3)
C6—C71.482 (3)O2—H2A0.80 (3)
C8—C91.480 (3)
C8—N1—N2109.60 (16)C11—C10—C9119.3 (2)
C8—N1—C15133.55 (17)C12—C11—C10121.2 (3)
N2—N1—C15116.84 (15)C12—C11—H11A119.4
C7—N2—N1103.59 (15)C10—C11—H11A119.4
C8—N3—C7104.99 (16)C11—C12—C13120.6 (3)
O2—C1—C2117.2 (2)C11—C12—H12A119.7
O2—C1—C6122.65 (19)C13—C12—H12A119.7
C2—C1—C6120.2 (2)C14—C13—C12118.9 (3)
C3—C2—C1120.3 (2)C14—C13—H13A120.5
C3—C2—H2C119.9C12—C13—H13A120.5
C1—C2—H2C119.9C13—C14—C9121.8 (3)
C4—C3—C2120.6 (2)C13—C14—H14A119.1
C4—C3—H3B119.7C9—C14—H14A119.1
C2—C3—H3B119.7C20—C15—C16118.40 (19)
C3—C4—C5119.7 (2)C20—C15—N1120.51 (19)
C3—C4—H4A120.2C16—C15—N1121.03 (19)
C5—C4—H4A120.2C17—C16—C15121.3 (2)
C4—C5—C6121.0 (2)C17—C16—Cl2119.75 (17)
C4—C5—H5A119.5C15—C16—Cl2118.97 (16)
C6—C5—H5A119.5C16—C17—C18118.2 (2)
C5—C6—C1118.25 (19)C16—C17—H17A120.9
C5—C6—C7120.75 (19)C18—C17—H17A120.9
C1—C6—C7120.97 (18)C19—C18—C17122.1 (2)
N2—C7—N3113.35 (17)C19—C18—Cl3119.10 (19)
N2—C7—C6121.76 (18)C17—C18—Cl3118.77 (18)
N3—C7—C6124.89 (17)C18—C19—C20118.7 (2)
N3—C8—N1108.46 (17)C18—C19—H19A120.7
N3—C8—C9123.73 (18)C20—C19—H19A120.7
N1—C8—C9127.77 (19)C19—C20—C15121.3 (2)
C14—C9—C10118.1 (2)C19—C20—Cl1119.44 (19)
C14—C9—C8123.0 (2)C15—C20—Cl1119.25 (17)
C10—C9—C8118.8 (2)C10—O1—H1A109 (2)
O1—C10—C11117.4 (2)C1—O2—H2A110.6 (19)
O1—C10—C9123.3 (2)
C8—N1—N2—C70.1 (2)C14—C9—C10—O1177.2 (2)
C15—N1—N2—C7−179.52 (17)C8—C9—C10—O1−4.5 (3)
O2—C1—C2—C3−178.7 (2)C14—C9—C10—C11−2.7 (3)
C6—C1—C2—C30.9 (4)C8—C9—C10—C11175.6 (2)
C1—C2—C3—C4−0.8 (4)O1—C10—C11—C12−179.0 (3)
C2—C3—C4—C50.2 (4)C9—C10—C11—C120.9 (4)
C3—C4—C5—C60.2 (4)C10—C11—C12—C131.9 (5)
C4—C5—C6—C10.0 (3)C11—C12—C13—C14−2.6 (5)
C4—C5—C6—C7177.9 (2)C12—C13—C14—C90.7 (5)
O2—C1—C6—C5179.0 (2)C10—C9—C14—C132.0 (4)
C2—C1—C6—C5−0.6 (3)C8—C9—C14—C13−176.3 (3)
O2—C1—C6—C71.1 (3)C8—N1—C15—C20−100.5 (3)
C2—C1—C6—C7−178.4 (2)N2—N1—C15—C2079.1 (2)
N1—N2—C7—N3−0.2 (2)C8—N1—C15—C1682.6 (3)
N1—N2—C7—C6179.23 (17)N2—N1—C15—C16−97.8 (2)
C8—N3—C7—N20.2 (2)C20—C15—C16—C171.3 (3)
C8—N3—C7—C6−179.23 (18)N1—C15—C16—C17178.30 (19)
C5—C6—C7—N2−177.3 (2)C20—C15—C16—Cl2−178.83 (16)
C1—C6—C7—N20.6 (3)N1—C15—C16—Cl2−1.8 (3)
C5—C6—C7—N32.1 (3)C15—C16—C17—C18−0.7 (3)
C1—C6—C7—N3179.90 (19)Cl2—C16—C17—C18179.45 (17)
C7—N3—C8—N1−0.1 (2)C16—C17—C18—C19−0.5 (4)
C7—N3—C8—C9−178.01 (19)C16—C17—C18—Cl3−179.86 (17)
N2—N1—C8—N30.0 (2)C17—C18—C19—C201.0 (4)
C15—N1—C8—N3179.5 (2)Cl3—C18—C19—C20−179.63 (19)
N2—N1—C8—C9177.80 (19)C18—C19—C20—C15−0.3 (4)
C15—N1—C8—C9−2.6 (4)C18—C19—C20—Cl1179.26 (19)
N3—C8—C9—C14−176.2 (2)C16—C15—C20—C19−0.8 (3)
N1—C8—C9—C146.3 (4)N1—C15—C20—C19−177.8 (2)
N3—C8—C9—C105.6 (3)C16—C15—C20—Cl1179.62 (16)
N1—C8—C9—C10−172.0 (2)N1—C15—C20—Cl12.6 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1A···N30.83 (3)1.89 (3)2.640 (3)149 (3)
O2—H2A···N20.81 (2)1.94 (2)2.648 (3)146 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2398).

References

  • Nisbet-Brown, E., Olivieri, N. F., Giardina, P. J., Grady, R. W., Neufeld, E. J., Sechaud, R., Krebs-Brown, A. J., Anderson, J. R., Alberti, D., Sizer, K. C. & Nathan, D. G. (2003). Lancet, 361, 1597–1602. [PubMed]
  • Rigaku (2005). CrystalClear Version 1.4.0. Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Steinhauser, S., Heinz, U., Bartholomä, M., Weyhermüller, T., Nick, H. & Hegetschweiler, K. (2004). Eur. J. Inorg. Chem. pp. 4177–4192.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography