4-(4-Chloro­phen­yl)-3-phenyl-5-(4-pyri­dyl)-4H-1,2,4-triazole

The title compound, C₁₉H₁₃ClN₄, was synthesized by the condensation of isonicotinohydrazide and N-(4-clorophen­yl)benzimidoyl chloride in N,N-dimethyl­acetamide. In the title mol­ecule, the triazole ring is oriented at dihedral angles of 34.64 (2), 30.97 (3) and 71.82 (3)° with respect to the pyridyl, phenyl and chloro­phenyl rings, respectively.

Key indicators

• Single-crystal X-ray study
• T = 113 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.045
• wR factor = 0.104
• Data-to-parameter ratio = 18.1

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S1. Comment

In recent years, the 1,2,4-triazole derivatives have appealed much attention by their structures, specific magnetic (Zhu et al., 2000; Zhu et al., 2001) and electron-transporting properties (Kido et al., 1993; Li et al., 2006). We report herein the crystal structure of the title compound, (I), in order to elucidate its molecular conformation.

In the molecule of (I) (Fig. 1), the bond lengths and angles are within normal ranges (Allen et al., 1987). Rings A (C1—C6), B (N1/N2/N3/C7/C8), C (N4/C9—C13) and D (C14—C19) are, of course, planar and the dihedral angles between them are A/B = 71.82 (3)°, A/C = 62.87 (3)°, A/D = 68.98 (2)°, B/C = 34.64 (2)°, B/D = 30.97 (3)° and C/D = 62.71 (3)°.

Related literature

For related literature, see: Kido et al. (1993); Li et al. (2006); Zhu et al. (2000); Zhu et al. (2001). For bond-length data, see: Allen et al. (1987).

S2. Experimental

The title compound was synthesized by the reaction of isonicotinohydrazide (274.0 mg, 2.0 mmol) and N-(4-clorophenyl)-benzimidoyl chloride (500.0 mg, 2.0 mmol) in N,N-dimethyl-acetamide (10 ml). The mixture was stirred and refluxed for 5 h. After cooling, the product crystallized from the orange reaction mixture. It was filtered off, washed with N,N-dimethyl-acetamide and dried in vacuo to give the product as fine colorless needles. Single crystals of (I) were obtained by slow evaporation of the ethanol solution in 15 d (yield; 385.0 mg, 57%, m.p. 488–489 K).

S3. Refinement

H atoms were positioned geometrically, with C—H = 0.95 Å for aromatic H atoms and constrained to ride on their parent atoms, with U_iso(H) = 1.2U_eq(C).

Computing details

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CrystalStructure (Rigaku/MSC, 2004); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2004).

Figures

Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

4-(4-Chlorophenyl)-3-phenyl-5-(4-pyridyl)-4H-1,2,4-triazole

Crystal data

C19H13ClN4	F(000) = 688
Mr = 332.78	Dx = 1.448 Mg m^−3
Monoclinic, P21/n	Melting point: 488 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71070 Å
a = 5.6436 (8) Å	Cell parameters from 3105 reflections
b = 16.730 (2) Å	θ = 1.8–25.0°
c = 16.239 (2) Å	µ = 0.26 mm^−1
β = 95.193 (7)°	T = 113 K
V = 1527.0 (3) Å^3	Prism, colorless
Z = 4	0.32 × 0.28 × 0.10 mm

Data collection

Rigaku Saturn diffractometer	3939 independent reflections
Radiation source: rotating anode	3204 reflections with I > 2σ(I)
Confocal monochromator	Rint = 0.041
Detector resolution: 7.31 pixels mm^-1	θmax = 28.7°, θmin = 1.8°
ω scans	h = −7→7
Absorption correction: multi-scan (Jacobson; 1998)	k = −22→22
Tmin = 0.912, Tmax = 0.975	l = −21→21
19621 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.104	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0442P)^2 + 0.487P] where P = (Fo^2 + 2Fc^2)/3
3939 reflections	(Δ/σ)max < 0.001
218 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.49 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	0.04399 (10)	0.03869 (2)	−0.12216 (3)	0.03717 (14)
N1	0.0462 (2)	0.27192 (7)	0.15171 (7)	0.0170 (3)
N2	0.1492 (2)	0.37831 (8)	0.22700 (8)	0.0217 (3)
N3	−0.0129 (2)	0.33435 (8)	0.26789 (8)	0.0219 (3)
N4	0.6710 (3)	0.41964 (8)	−0.01248 (9)	0.0261 (3)
C1	0.0402 (3)	0.21366 (8)	0.08607 (9)	0.0168 (3)
C2	−0.1579 (3)	0.20819 (9)	0.02902 (9)	0.0193 (3)
H2	−0.2925	0.2413	0.0342	0.023*
C3	−0.1572 (3)	0.15387 (9)	−0.03561 (10)	0.0225 (3)
H3	−0.2911	0.1493	−0.0752	0.027*
C4	0.0415 (3)	0.10650 (9)	−0.04141 (9)	0.0228 (3)
C5	0.2388 (3)	0.11159 (9)	0.01555 (10)	0.0242 (4)
H5	0.3732	0.0784	0.0104	0.029*
C6	0.2378 (3)	0.16572 (9)	0.08021 (10)	0.0203 (3)
H6	0.3713	0.1698	0.1200	0.024*
C7	0.1828 (3)	0.34010 (8)	0.15814 (9)	0.0180 (3)
C8	−0.0723 (3)	0.27118 (9)	0.22224 (9)	0.0179 (3)
C9	0.3466 (3)	0.36720 (9)	0.09792 (9)	0.0185 (3)
C10	0.2993 (3)	0.35674 (9)	0.01233 (10)	0.0207 (3)
H10	0.1561	0.3319	−0.0098	0.025*
C11	0.4652 (3)	0.38327 (9)	−0.03956 (10)	0.0222 (3)
H11	0.4319	0.3754	−0.0974	0.027*
C12	0.7103 (3)	0.43173 (9)	0.07007 (10)	0.0231 (3)
H12	0.8514	0.4589	0.0905	0.028*
C13	0.5552 (3)	0.40652 (9)	0.12651 (10)	0.0210 (3)
H13	0.5911	0.4160	0.1840	0.025*
C14	−0.2430 (3)	0.21041 (9)	0.24557 (9)	0.0181 (3)
C15	−0.4253 (3)	0.23521 (9)	0.29282 (9)	0.0216 (3)
H15	−0.4386	0.2899	0.3075	0.026*
C16	−0.5866 (3)	0.17960 (10)	0.31825 (10)	0.0242 (3)
H16	−0.7085	0.1967	0.3509	0.029*
C17	−0.5729 (3)	0.10054 (10)	0.29707 (10)	0.0229 (3)
H17	−0.6851	0.0633	0.3145	0.028*
C18	−0.3944 (3)	0.07550 (10)	0.25005 (10)	0.0236 (3)
H18	−0.3855	0.0209	0.2347	0.028*
C19	−0.2272 (3)	0.12954 (9)	0.22487 (9)	0.0203 (3)
H19	−0.1030	0.1115	0.1937	0.024*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0690 (4)	0.0219 (2)	0.0225 (2)	−0.0056 (2)	0.0144 (2)	−0.00746 (16)
N1	0.0189 (7)	0.0167 (6)	0.0154 (6)	0.0013 (5)	0.0018 (5)	−0.0014 (5)
N2	0.0240 (7)	0.0208 (6)	0.0204 (7)	0.0018 (5)	0.0026 (6)	−0.0020 (5)
N3	0.0239 (7)	0.0215 (6)	0.0203 (6)	0.0017 (5)	0.0032 (5)	−0.0029 (5)
N4	0.0258 (8)	0.0235 (7)	0.0295 (8)	0.0034 (6)	0.0058 (6)	0.0021 (6)
C1	0.0215 (8)	0.0152 (6)	0.0141 (7)	−0.0013 (6)	0.0048 (6)	−0.0006 (5)
C2	0.0205 (8)	0.0193 (7)	0.0183 (7)	0.0015 (6)	0.0028 (6)	0.0018 (6)
C3	0.0286 (9)	0.0220 (8)	0.0165 (7)	−0.0068 (6)	0.0004 (6)	0.0021 (6)
C4	0.0376 (10)	0.0159 (7)	0.0164 (7)	−0.0045 (7)	0.0099 (7)	−0.0018 (6)
C5	0.0283 (9)	0.0194 (7)	0.0267 (8)	0.0029 (6)	0.0111 (7)	0.0003 (6)
C6	0.0199 (8)	0.0207 (7)	0.0208 (7)	0.0012 (6)	0.0042 (6)	0.0010 (6)
C7	0.0208 (8)	0.0160 (7)	0.0170 (7)	0.0016 (6)	0.0002 (6)	−0.0001 (5)
C8	0.0193 (8)	0.0198 (7)	0.0145 (7)	0.0056 (6)	0.0020 (6)	0.0003 (5)
C9	0.0211 (8)	0.0144 (7)	0.0199 (7)	0.0025 (6)	0.0019 (6)	0.0003 (5)
C10	0.0217 (8)	0.0201 (7)	0.0200 (7)	0.0001 (6)	0.0010 (6)	−0.0002 (6)
C11	0.0247 (9)	0.0225 (8)	0.0196 (7)	0.0034 (6)	0.0024 (6)	0.0006 (6)
C12	0.0199 (8)	0.0192 (7)	0.0303 (9)	0.0025 (6)	0.0020 (7)	0.0019 (6)
C13	0.0232 (8)	0.0178 (7)	0.0215 (8)	0.0019 (6)	−0.0012 (6)	0.0002 (6)
C14	0.0179 (8)	0.0219 (7)	0.0145 (7)	0.0025 (6)	0.0010 (6)	0.0010 (6)
C15	0.0233 (9)	0.0245 (8)	0.0171 (7)	0.0063 (6)	0.0031 (6)	−0.0002 (6)
C16	0.0208 (8)	0.0333 (9)	0.0191 (8)	0.0054 (7)	0.0060 (6)	0.0024 (6)
C17	0.0197 (8)	0.0282 (8)	0.0212 (8)	−0.0014 (7)	0.0034 (6)	0.0072 (6)
C18	0.0255 (9)	0.0232 (8)	0.0221 (8)	0.0014 (6)	0.0015 (7)	0.0037 (6)
C19	0.0220 (8)	0.0211 (7)	0.0180 (7)	0.0050 (6)	0.0038 (6)	0.0017 (6)

Geometric parameters (Å, º)

Cl1—C4	1.7350 (15)	C8—C14	1.473 (2)
N1—C7	1.3756 (19)	C9—C13	1.391 (2)
N1—C8	1.3776 (19)	C9—C10	1.402 (2)
N1—C1	1.4425 (18)	C10—C11	1.388 (2)
N2—C7	1.3166 (19)	C10—H10	0.9500
N2—N3	1.3887 (18)	C11—H11	0.9500
N3—C8	1.3169 (19)	C12—C13	1.389 (2)
N4—C11	1.349 (2)	C12—H12	0.9500
N4—C12	1.354 (2)	C13—H13	0.9500
C1—C6	1.384 (2)	C14—C19	1.399 (2)
C1—C2	1.389 (2)	C14—C15	1.401 (2)
C2—C3	1.389 (2)	C15—C16	1.390 (2)
C2—H2	0.9500	C15—H15	0.9500
C3—C4	1.384 (2)	C16—C17	1.371 (2)
C3—H3	0.9500	C16—H16	0.9500
C4—C5	1.384 (2)	C17—C18	1.383 (2)
C5—C6	1.387 (2)	C17—H17	0.9500
C5—H5	0.9500	C18—C19	1.394 (2)
C6—H6	0.9500	C18—H18	0.9500
C7—C9	1.476 (2)	C19—H19	0.9500
C7—N1—C8	104.79 (12)	C10—C9—C7	122.95 (14)
C7—N1—C1	126.29 (12)	C11—C10—C9	118.93 (15)
C8—N1—C1	128.88 (12)	C11—C10—H10	120.5
C7—N2—N3	107.49 (12)	C9—C10—H10	120.5
C8—N3—N2	107.53 (12)	N4—C11—C10	123.67 (15)
C11—N4—C12	116.69 (14)	N4—C11—H11	118.2
C6—C1—C2	121.40 (14)	C10—C11—H11	118.2
C6—C1—N1	118.50 (14)	N4—C12—C13	123.46 (15)
C2—C1—N1	120.07 (13)	N4—C12—H12	118.3
C3—C2—C1	119.37 (15)	C13—C12—H12	118.3
C3—C2—H2	120.3	C12—C13—C9	119.22 (15)
C1—C2—H2	120.3	C12—C13—H13	120.4
C4—C3—C2	118.93 (15)	C9—C13—H13	120.4
C4—C3—H3	120.5	C19—C14—C15	118.95 (14)
C2—C3—H3	120.5	C19—C14—C8	123.24 (13)
C3—C4—C5	121.82 (14)	C15—C14—C8	117.78 (13)
C3—C4—Cl1	119.20 (13)	C16—C15—C14	119.83 (14)
C5—C4—Cl1	118.97 (13)	C16—C15—H15	120.1
C4—C5—C6	119.22 (15)	C14—C15—H15	120.1
C4—C5—H5	120.4	C17—C16—C15	121.20 (15)
C6—C5—H5	120.4	C17—C16—H16	119.4
C1—C6—C5	119.25 (15)	C15—C16—H16	119.4
C1—C6—H6	120.4	C16—C17—C18	119.42 (15)
C5—C6—H6	120.4	C16—C17—H17	120.3
N2—C7—N1	110.14 (13)	C18—C17—H17	120.3
N2—C7—C9	124.07 (13)	C17—C18—C19	120.77 (15)
N1—C7—C9	125.78 (13)	C17—C18—H18	119.6
N3—C8—N1	110.04 (13)	C19—C18—H18	119.6
N3—C8—C14	123.24 (13)	C18—C19—C14	119.81 (14)
N1—C8—C14	126.71 (13)	C18—C19—H19	120.1
C13—C9—C10	117.97 (14)	C14—C19—H19	120.1
C13—C9—C7	119.06 (14)
C7—N2—N3—C8	−0.17 (17)	C1—N1—C8—C14	−2.4 (2)
C7—N1—C1—C6	69.64 (19)	N2—C7—C9—C13	33.6 (2)
C8—N1—C1—C6	−107.64 (18)	N1—C7—C9—C13	−145.59 (15)
C7—N1—C1—C2	−108.42 (17)	N2—C7—C9—C10	−144.90 (16)
C8—N1—C1—C2	74.3 (2)	N1—C7—C9—C10	35.9 (2)
C6—C1—C2—C3	−0.4 (2)	C13—C9—C10—C11	2.2 (2)
N1—C1—C2—C3	177.58 (13)	C7—C9—C10—C11	−179.20 (14)
C1—C2—C3—C4	0.0 (2)	C12—N4—C11—C10	−1.6 (2)
C2—C3—C4—C5	0.3 (2)	C9—C10—C11—N4	−0.6 (2)
C2—C3—C4—Cl1	−179.82 (11)	C11—N4—C12—C13	2.1 (2)
C3—C4—C5—C6	−0.1 (2)	N4—C12—C13—C9	−0.5 (2)
Cl1—C4—C5—C6	179.97 (12)	C10—C9—C13—C12	−1.7 (2)
C2—C1—C6—C5	0.6 (2)	C7—C9—C13—C12	179.66 (13)
N1—C1—C6—C5	−177.46 (13)	N3—C8—C14—C19	−147.90 (16)
C4—C5—C6—C1	−0.3 (2)	N1—C8—C14—C19	32.6 (2)
N3—N2—C7—N1	0.34 (17)	N3—C8—C14—C15	30.2 (2)
N3—N2—C7—C9	−179.00 (14)	N1—C8—C14—C15	−149.32 (15)
C8—N1—C7—N2	−0.37 (17)	C19—C14—C15—C16	0.0 (2)
C1—N1—C7—N2	−178.18 (14)	C8—C14—C15—C16	−178.22 (14)
C8—N1—C7—C9	178.95 (14)	C14—C15—C16—C17	−0.8 (2)
C1—N1—C7—C9	1.1 (2)	C15—C16—C17—C18	0.5 (2)
N2—N3—C8—N1	−0.06 (17)	C16—C17—C18—C19	0.7 (2)
N2—N3—C8—C14	−179.67 (13)	C17—C18—C19—C14	−1.5 (2)
C7—N1—C8—N3	0.26 (17)	C15—C14—C19—C18	1.2 (2)
C1—N1—C8—N3	177.99 (14)	C8—C14—C19—C18	179.28 (15)
C7—N1—C8—C14	179.85 (14)