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In the title compound, C20H15ClN4O, the meth­oxy- and chloro­phenyl rings form dihedral angles of 63.2 (1) and 31.1 (1)°, respectively, with the triazole ring, and the dihedral angle between the triazole and pyridine rings is 35.1 (1)°. Centrosymmetrically related mol­ecules are linked together by weak C—H...N hydrogen bonds, forming a dimer.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680705547X/ci2502sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680705547X/ci2502Isup2.hkl
Contains datablock I

CCDC reference: 672887

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.045
  • wR factor = 0.130
  • Data-to-parameter ratio = 14.5

checkCIF/PLATON results

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Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) 400 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

In the title molecule (Fig. 1), the pyridine and benzene rings lie in a propeller arrangement around the central 1,2,4-triazole ring, thereby minimizing the steric effects among these rings. The dihedral angles between the pyridine ring and the two benzene rings (C8—C13 and C15—C20) are 58.4 (1) and 65.4 (1)°, respectively. These two benzene rings form dihedral angles of 63.2 (1) and 31.1 (1)°, respectively, with the triazole ring, and the dihedral angle between the triazole ring and the pyridine ring is 35.1 (1)°.

In the crystal structure, molecules related by a center of symmetry are linked by C—H···N hydrogen bonds (Table 1), forming a dimer.

Related literature top

For the structural details of 4-(4-methoxyphenyl)-3-(2-pyridyl)-5-(4-methylphenyl)-4H-1,2,4-triazole, see: Zhang et al. (2006).

Experimental top

The title compound was synthesized according to a literature method (Zhang et al., 2006). Equivalent amounts of p-methoxyphosphazoanilide and N-pyridyl-N'-p-chlorophenylhydrazine were reacted in ethanol (15 ml) for 1 h. After allowing the resulting solution to stand in air for 15 d, colourless crystals were formed on slow evaporation of the solvent. The crystals were isolated, washed with ethanol and dried.

Refinement top

H atoms were placed in idealized positions (C—H = 0.93 or 0.96 Å) and constrained to ride on their parent atoms, with Uiso(H) = 1.2 or 1.5(methyl) Ueq(C).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with atomic numbering. Displacement ellipsoids are drawn at the 30% probability level.
5-(4-Chlorophenyl)-4-(4-methoxyphenyl)-3-(2-pyridyl)-4H-1,2,4-triazole top
Crystal data top
C20H15ClN4OZ = 2
Mr = 362.81F(000) = 376
Triclinic, P1Dx = 1.367 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.808 (4) ÅCell parameters from 1472 reflections
b = 10.083 (4) Åθ = 4.2–28.3°
c = 10.274 (4) ŵ = 0.23 mm1
α = 70.415 (5)°T = 298 K
β = 73.417 (6)°Block, colourless
γ = 69.768 (6)°0.15 × 0.15 × 0.10 mm
V = 881.5 (6) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
3411 independent reflections
Radiation source: fine-focus sealed tube2757 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
ϕ and ω scansθmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1212
Tmin = 0.966, Tmax = 0.977k = 1211
6776 measured reflectionsl = 1212
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.062P)2 + 0.1955P]
where P = (Fo2 + 2Fc2)/3
3411 reflections(Δ/σ)max = 0.001
236 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.24 e Å3
Crystal data top
C20H15ClN4Oγ = 69.768 (6)°
Mr = 362.81V = 881.5 (6) Å3
Triclinic, P1Z = 2
a = 9.808 (4) ÅMo Kα radiation
b = 10.083 (4) ŵ = 0.23 mm1
c = 10.274 (4) ÅT = 298 K
α = 70.415 (5)°0.15 × 0.15 × 0.10 mm
β = 73.417 (6)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
3411 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2757 reflections with I > 2σ(I)
Tmin = 0.966, Tmax = 0.977Rint = 0.019
6776 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.130H-atom parameters constrained
S = 1.05Δρmax = 0.19 e Å3
3411 reflectionsΔρmin = 0.24 e Å3
236 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
xyzUiso*/Ueq
C10.3198 (2)0.0397 (2)0.83095 (19)0.0450 (4)
C20.3227 (2)0.0760 (2)1.0498 (2)0.0444 (4)
C30.2817 (2)0.1236 (2)1.2046 (2)0.0467 (5)
C40.3906 (3)0.1979 (3)1.2842 (3)0.0661 (6)
H120.49010.21881.24120.079*
C50.3496 (4)0.2400 (3)1.4270 (3)0.0842 (8)
H130.42080.28991.48320.101*
C60.2020 (4)0.2079 (3)1.4866 (3)0.0823 (8)
H140.17130.23361.58390.099*
C70.1004 (3)0.1368 (3)1.3999 (2)0.0706 (7)
H150.00030.11761.44090.085*
C80.12017 (19)0.15735 (19)1.00964 (17)0.0381 (4)
C90.0141 (2)0.18012 (19)0.97612 (18)0.0408 (4)
H220.02060.12880.91890.049*
C100.1389 (2)0.27883 (19)1.02726 (19)0.0429 (4)
H210.22950.29461.00470.052*
C110.1277 (2)0.35414 (19)1.11251 (19)0.0435 (4)
C120.0091 (2)0.3351 (2)1.1402 (2)0.0489 (5)
H190.01680.38931.19400.059*
C130.1335 (2)0.2371 (2)1.08900 (19)0.0449 (4)
H180.22520.22481.10760.054*
C140.3877 (3)0.4630 (3)1.1557 (3)0.0857 (8)
H23A0.39590.51081.05910.128*
H23B0.46120.52041.21490.128*
H23C0.40290.36781.18080.128*
C150.2846 (2)0.1481 (2)0.69997 (19)0.0445 (4)
C160.3221 (2)0.1024 (2)0.5780 (2)0.0571 (5)
H50.36100.00300.58290.069*
C170.3029 (3)0.2014 (3)0.4497 (2)0.0628 (6)
H60.32940.16940.36860.075*
C180.2441 (2)0.3477 (3)0.4434 (2)0.0545 (5)
C190.2046 (2)0.3961 (2)0.5624 (2)0.0568 (5)
H20.16380.49550.55710.068*
C200.2259 (2)0.2966 (2)0.6897 (2)0.0515 (5)
H30.20050.32960.77010.062*
Cl10.22050 (7)0.47545 (8)0.28259 (6)0.0782 (2)
N10.43195 (19)0.07819 (18)0.83541 (18)0.0565 (5)
N20.43441 (18)0.15167 (18)0.97501 (18)0.0557 (5)
N30.24694 (16)0.04656 (16)0.96486 (15)0.0406 (4)
N40.13735 (19)0.0939 (2)1.26017 (17)0.0568 (5)
O10.24465 (16)0.44833 (16)1.17406 (16)0.0624 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0438 (10)0.0449 (10)0.0438 (10)0.0108 (8)0.0011 (8)0.0162 (8)
C20.0420 (10)0.0416 (10)0.0485 (10)0.0104 (8)0.0115 (8)0.0094 (8)
C30.0534 (11)0.0420 (10)0.0474 (11)0.0160 (8)0.0153 (9)0.0076 (8)
C40.0681 (14)0.0651 (14)0.0683 (15)0.0242 (12)0.0315 (12)0.0003 (12)
C50.109 (2)0.0849 (19)0.0684 (16)0.0380 (17)0.0533 (16)0.0093 (14)
C60.127 (3)0.0809 (18)0.0454 (13)0.0469 (18)0.0237 (15)0.0002 (12)
C70.0814 (17)0.0750 (16)0.0487 (13)0.0270 (13)0.0035 (12)0.0097 (11)
C80.0412 (9)0.0375 (9)0.0325 (8)0.0091 (7)0.0044 (7)0.0093 (7)
C90.0501 (10)0.0400 (10)0.0350 (9)0.0131 (8)0.0111 (8)0.0103 (7)
C100.0433 (10)0.0409 (10)0.0421 (10)0.0087 (8)0.0123 (8)0.0075 (8)
C110.0475 (10)0.0371 (9)0.0399 (9)0.0070 (8)0.0052 (8)0.0103 (8)
C120.0579 (12)0.0497 (11)0.0470 (11)0.0149 (9)0.0101 (9)0.0226 (9)
C130.0433 (10)0.0518 (11)0.0443 (10)0.0137 (8)0.0118 (8)0.0152 (9)
C140.0478 (13)0.0877 (19)0.120 (2)0.0103 (12)0.0154 (14)0.0554 (17)
C150.0420 (10)0.0486 (11)0.0406 (10)0.0118 (8)0.0003 (8)0.0165 (8)
C160.0609 (13)0.0566 (13)0.0519 (12)0.0084 (10)0.0049 (10)0.0251 (10)
C170.0655 (14)0.0820 (16)0.0425 (11)0.0179 (12)0.0036 (10)0.0265 (11)
C180.0482 (11)0.0711 (14)0.0417 (11)0.0213 (10)0.0076 (8)0.0078 (10)
C190.0639 (13)0.0501 (12)0.0500 (12)0.0146 (10)0.0065 (10)0.0100 (10)
C200.0614 (12)0.0506 (12)0.0399 (10)0.0146 (9)0.0029 (9)0.0154 (9)
Cl10.0825 (4)0.1001 (5)0.0479 (3)0.0364 (4)0.0219 (3)0.0050 (3)
N10.0539 (10)0.0480 (10)0.0529 (10)0.0048 (8)0.0011 (8)0.0139 (8)
N20.0507 (10)0.0461 (9)0.0576 (10)0.0044 (8)0.0077 (8)0.0093 (8)
N30.0401 (8)0.0403 (8)0.0394 (8)0.0079 (6)0.0075 (6)0.0114 (6)
N40.0585 (11)0.0623 (11)0.0445 (9)0.0164 (9)0.0095 (8)0.0085 (8)
O10.0557 (9)0.0583 (9)0.0712 (10)0.0017 (7)0.0065 (7)0.0339 (8)
Geometric parameters (Å, º) top
C1—N11.309 (2)C10—H210.93
C1—N31.370 (2)C11—O11.361 (2)
C1—C151.464 (3)C11—C121.385 (3)
C2—N21.307 (2)C12—C131.375 (3)
C2—N31.361 (2)C12—H190.93
C2—C31.476 (3)C13—H180.93
C3—N41.334 (3)C14—O11.419 (3)
C3—C41.381 (3)C14—H23A0.96
C4—C51.363 (4)C14—H23B0.96
C4—H120.93C14—H23C0.96
C5—C61.370 (4)C15—C201.384 (3)
C5—H130.93C15—C161.387 (3)
C6—C71.373 (4)C16—C171.378 (3)
C6—H140.93C16—H50.93
C7—N41.332 (3)C17—C181.372 (3)
C7—H150.93C17—H60.93
C8—C131.379 (3)C18—C191.372 (3)
C8—C91.380 (3)C18—Cl11.740 (2)
C8—N31.436 (2)C19—C201.375 (3)
C9—C101.380 (2)C19—H20.93
C9—H220.93C20—H30.93
C10—C111.384 (3)N1—N21.379 (2)
N1—C1—N3109.87 (17)C11—C12—H19119.6
N1—C1—C15123.48 (17)C12—C13—C8118.90 (18)
N3—C1—C15126.62 (16)C12—C13—H18120.5
N2—C2—N3110.62 (17)C8—C13—H18120.5
N2—C2—C3123.71 (17)O1—C14—H23A109.5
N3—C2—C3125.59 (16)O1—C14—H23B109.5
N4—C3—C4123.3 (2)H23A—C14—H23B109.5
N4—C3—C2116.75 (17)O1—C14—H23C109.5
C4—C3—C2119.97 (19)H23A—C14—H23C109.5
C5—C4—C3118.7 (2)H23B—C14—H23C109.5
C5—C4—H12120.6C20—C15—C16118.10 (19)
C3—C4—H12120.6C20—C15—C1122.82 (17)
C4—C5—C6119.0 (2)C16—C15—C1118.88 (18)
C4—C5—H13120.5C17—C16—C15121.3 (2)
C6—C5—H13120.5C17—C16—H5119.3
C5—C6—C7118.7 (2)C15—C16—H5119.3
C5—C6—H14120.6C18—C17—C16119.05 (19)
C7—C6—H14120.6C18—C17—H6120.5
N4—C7—C6123.5 (2)C16—C17—H6120.5
N4—C7—H15118.2C19—C18—C17121.0 (2)
C6—C7—H15118.2C19—C18—Cl1118.90 (18)
C13—C8—C9120.80 (16)C17—C18—Cl1120.10 (17)
C13—C8—N3119.40 (16)C18—C19—C20119.5 (2)
C9—C8—N3119.78 (15)C18—C19—H2120.3
C8—C9—C10120.17 (17)C20—C19—H2120.3
C8—C9—H22119.9C19—C20—C15121.07 (18)
C10—C9—H22119.9C19—C20—H3119.5
C9—C10—C11119.31 (18)C15—C20—H3119.5
C9—C10—H21120.3C1—N1—N2107.71 (15)
C11—C10—H21120.3C2—N2—N1107.13 (15)
O1—C11—C10124.12 (18)C2—N3—C1104.68 (15)
O1—C11—C12115.96 (17)C2—N3—C8126.39 (15)
C10—C11—C12119.92 (16)C1—N3—C8128.93 (15)
C13—C12—C11120.77 (17)C7—N4—C3116.75 (19)
C13—C12—H19119.6C11—O1—C14117.50 (17)
N2—C2—C3—N4142.6 (2)C17—C18—C19—C200.8 (3)
N3—C2—C3—N433.7 (3)Cl1—C18—C19—C20178.51 (16)
N2—C2—C3—C435.9 (3)C18—C19—C20—C150.9 (3)
N3—C2—C3—C4147.8 (2)C16—C15—C20—C190.3 (3)
N4—C3—C4—C51.8 (4)C1—C15—C20—C19175.11 (19)
C2—C3—C4—C5179.8 (2)N3—C1—N1—N20.1 (2)
C3—C4—C5—C60.3 (4)C15—C1—N1—N2177.91 (17)
C4—C5—C6—C71.3 (4)N3—C2—N2—N10.8 (2)
C5—C6—C7—N41.6 (4)C3—C2—N2—N1176.01 (18)
C13—C8—C9—C102.9 (3)C1—N1—N2—C20.5 (2)
N3—C8—C9—C10175.30 (15)N2—C2—N3—C10.8 (2)
C8—C9—C10—C110.1 (3)C3—C2—N3—C1175.99 (18)
C9—C10—C11—O1176.64 (17)N2—C2—N3—C8178.47 (17)
C9—C10—C11—C123.0 (3)C3—C2—N3—C84.8 (3)
O1—C11—C12—C13176.80 (17)N1—C1—N3—C20.4 (2)
C10—C11—C12—C132.9 (3)C15—C1—N3—C2178.31 (18)
C11—C12—C13—C80.2 (3)N1—C1—N3—C8178.80 (18)
C9—C8—C13—C123.1 (3)C15—C1—N3—C80.9 (3)
N3—C8—C13—C12175.17 (16)C13—C8—N3—C262.1 (2)
N1—C1—C15—C20145.4 (2)C9—C8—N3—C2116.2 (2)
N3—C1—C15—C2032.2 (3)C13—C8—N3—C1117.0 (2)
N1—C1—C15—C1629.4 (3)C9—C8—N3—C164.8 (3)
N3—C1—C15—C16153.0 (2)C6—C7—N4—C30.2 (4)
C20—C15—C16—C170.5 (3)C4—C3—N4—C71.6 (3)
C1—C15—C16—C17174.54 (19)C2—C3—N4—C7179.95 (19)
C15—C16—C17—C180.6 (3)C10—C11—O1—C143.8 (3)
C16—C17—C18—C190.0 (3)C12—C11—O1—C14175.9 (2)
C16—C17—C18—Cl1179.26 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H22···N4i0.932.603.454 (3)154
Symmetry code: (i) x, y, z+2.

Experimental details

Crystal data
Chemical formulaC20H15ClN4O
Mr362.81
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)9.808 (4), 10.083 (4), 10.274 (4)
α, β, γ (°)70.415 (5), 73.417 (6), 69.768 (6)
V3)881.5 (6)
Z2
Radiation typeMo Kα
µ (mm1)0.23
Crystal size (mm)0.15 × 0.15 × 0.10
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.966, 0.977
No. of measured, independent and
observed [I > 2σ(I)] reflections
6776, 3411, 2757
Rint0.019
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.130, 1.05
No. of reflections3411
No. of parameters236
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.19, 0.24

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H22···N4i0.932.603.454 (3)154
Symmetry code: (i) x, y, z+2.
 

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