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

Gong, X.; Wang, Z.; Liu, Y.

doi:10.1107/S1600536809049174

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3214

doi:10.1107/S1600536809049174

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

Xiaoning Gong,^a Zuoxiang Wang ^a ^* and Yan Liu ^a

^aSchool of Chemistry and Engineering, Southeast University, Nanjing 211189, People's Republic of China
^*Correspondence e-mail: wangzx0908@yahoo.com.cn

(Received 4 November 2009; accepted 18 November 2009; online 25 November 2009)

In the title compound, C₂₀H₁₆N₄, the m-tolyl and phenyl substituents form dihedral angles of 74.20 (6) and 36.94 (8)°, respectively, with the 1,2,4-triazole ring and the dihedral angle between the triazole and pyridine rings is 36.06 (9)°. In the crystal, molecules are linked by C—H⋯N and C—H⋯π interactions.

Related literature

For the synthesis of the title compound, see: Klingsberg (1958 ). For related structures, see: Wang et al. (2005 ); Huang et al. (2008 ).

Experimental

Crystal data

C₂₀H₁₆N₄
M_r = 312.37
Monoclinic, P 2₁ /c
a = 11.246 (3) Å
b = 9.377 (2) Å
c = 18.956 (5) Å
β = 124.655 (16)°
V = 1644.3 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.65 × 0.50 × 0.27 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.787, T_max = 1.000
16277 measured reflections
3751 independent reflections
2691 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.162
S = 1.06
3751 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯N2ⁱ	0.93	2.60	3.375 (3)	142
C20—H20A⋯N2ⁱⁱ	0.96	2.62	3.549 (4)	163
C10—H10⋯Cg1ⁱⁱ	0.93	2.72	3.646 (3)	175
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ . Cg1 is the centroid of the C3–C8 ring.

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; 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: PRPKAPPA (Ferguson, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809049174/gk2238sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809049174/gk2238Isup2.hkl

checkCIF report

Comment top

Recently we have prepared some new 1,2,4-triazoles and their complexes (Wang et al., 2005; Huang et al., 2008). We report here the crystal structure of the title compound.

Related literature top

For the synthesis of the title compound, see: Klingsberg (1958). For related structures, see: Wang et al. (2005); Huang et al. (2008). Cg1is the centroid of the C3–C8 ring.

Experimental top

The title compound was prepared by the reaction of 3,3^'– dimethylphenylphosphazoanilide (2.90, 12 mmol) with N-benzoyl-N^'-(2-pyridoyl)hydrazine (2.41 g, 10 mmol) in N,N-dimethylaniline at 463–473 K for 5 hrs (Klingsberg, 1958). Single crystals suitable for X-ray diffraction were obtained by recrystallization from water.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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: PRPKAPPA (Ferguson, 1999).

Figures top

Fig. 1. The molecular structure of the title compound with the atom labelling. Displacement ellipsoids are shown at the 30% probability level.

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

Crystal data top

C₂₀H₁₆N₄	F(000) = 656
M_r = 312.37	D_x = 1.262 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3426 reflections
a = 11.246 (3) Å	θ = 2.3–27.5°
b = 9.377 (2) Å	µ = 0.08 mm⁻¹
c = 18.956 (5) Å	T = 293 K
β = 124.655 (16)°	Block, white
V = 1644.3 (7) Å³	0.65 × 0.50 × 0.27 mm
Z = 4

Data collection top

Rigaku SCXmini diffractometer	3751 independent reflections
Radiation source: fine-focus sealed tube	2691 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
ω scan	θ_max = 27.5°, θ_min = 2.3°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	h = −14→14
T_min = 0.787, T_max = 1.000	k = −12→12
16277 measured reflections	l = −24→24

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.162	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0823P)² + 0.1727P] where P = (F_o² + 2F_c²)/3
3751 reflections	(Δ/σ)_max < 0.001
218 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₀H₁₆N₄	V = 1644.3 (7) Å³
M_r = 312.37	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.246 (3) Å	µ = 0.08 mm⁻¹
b = 9.377 (2) Å	T = 293 K
c = 18.956 (5) Å	0.65 × 0.50 × 0.27 mm
β = 124.655 (16)°

Data collection top

Rigaku SCXmini diffractometer	3751 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	2691 reflections with I > 2σ(I)
T_min = 0.787, T_max = 1.000	R_int = 0.040
16277 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.162	H-atom parameters constrained
S = 1.06	Δρ_max = 0.31 e Å⁻³
3751 reflections	Δρ_min = −0.23 e Å⁻³
218 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
C1	0.91724 (18)	−0.14398 (19)	0.88581 (11)	0.0461 (4)
C2	0.74890 (17)	−0.02378 (18)	0.77576 (11)	0.0447 (4)
C3	1.05742 (18)	−0.1952 (2)	0.95950 (11)	0.0481 (4)
C4	1.0759 (2)	−0.3404 (2)	0.97830 (14)	0.0603 (5)
H4	1.0017	−0.4038	0.9427	0.072*
C5	1.2038 (2)	−0.3906 (2)	1.04945 (15)	0.0703 (6)
H5	1.2151	−0.4876	1.0619	0.084*
C6	1.3143 (2)	−0.2978 (3)	1.10189 (14)	0.0684 (6)
H6	1.4005	−0.3317	1.1498	0.082*
C7	1.2969 (2)	−0.1545 (2)	1.08313 (12)	0.0618 (5)
H7	1.3719	−0.0917	1.1186	0.074*
C8	1.16981 (19)	−0.1029 (2)	1.01265 (11)	0.0513 (4)
H8	1.1594	−0.0058	1.0007	0.062*
C9	0.67146 (17)	0.07496 (19)	0.70258 (10)	0.0457 (4)
C10	0.6617 (2)	0.1881 (3)	0.59246 (13)	0.0687 (6)
H10	0.7040	0.2101	0.5636	0.082*
C11	0.5267 (2)	0.2440 (2)	0.56156 (13)	0.0679 (6)
H11	0.4792	0.3009	0.5127	0.081*
C12	0.4644 (2)	0.2140 (2)	0.60434 (13)	0.0625 (5)
H12	0.3740	0.2507	0.5852	0.075*
C13	0.53747 (18)	0.1287 (2)	0.67597 (12)	0.0529 (5)
H13	0.4973	0.1074	0.7062	0.063*
C14	1.00456 (17)	0.05403 (19)	0.83598 (10)	0.0445 (4)
C15	1.08632 (18)	−0.0030 (2)	0.80966 (11)	0.0510 (4)
H15	1.0713	−0.0967	0.7903	0.061*
C16	1.19103 (19)	0.0793 (2)	0.81200 (13)	0.0595 (5)
C17	1.2116 (2)	0.2171 (3)	0.84272 (14)	0.0676 (6)
H17	1.2815	0.2735	0.8447	0.081*
C18	1.1320 (2)	0.2735 (2)	0.87042 (13)	0.0693 (6)
H18	1.1494	0.3660	0.8917	0.083*
C19	1.0255 (2)	0.1913 (2)	0.86644 (12)	0.0583 (5)
H19	0.9695	0.2283	0.8840	0.070*
C20	1.2756 (3)	0.0194 (3)	0.7795 (2)	0.1004 (10)
H20A	1.2660	0.0814	0.7363	0.151*
H20B	1.2390	−0.0734	0.7555	0.151*
H20C	1.3757	0.0120	0.8262	0.151*
N1	0.68517 (15)	−0.12089 (17)	0.79297 (10)	0.0527 (4)
N2	0.79217 (16)	−0.19790 (17)	0.86336 (10)	0.0536 (4)
N3	0.89575 (14)	−0.03337 (15)	0.83260 (9)	0.0441 (3)
N4	0.73453 (16)	0.1044 (2)	0.66152 (10)	0.0615 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0450 (9)	0.0508 (9)	0.0478 (9)	−0.0015 (8)	0.0295 (8)	0.0013 (8)
C2	0.0375 (9)	0.0539 (9)	0.0450 (9)	−0.0015 (7)	0.0247 (8)	−0.0039 (8)
C3	0.0455 (9)	0.0578 (10)	0.0489 (9)	0.0031 (8)	0.0316 (8)	0.0057 (8)
C4	0.0523 (11)	0.0593 (12)	0.0703 (12)	−0.0002 (9)	0.0354 (10)	0.0096 (10)
C5	0.0653 (13)	0.0683 (13)	0.0807 (15)	0.0140 (11)	0.0436 (12)	0.0243 (12)
C6	0.0563 (12)	0.0908 (16)	0.0562 (11)	0.0201 (11)	0.0308 (10)	0.0193 (11)
C7	0.0533 (11)	0.0786 (14)	0.0473 (10)	0.0022 (10)	0.0250 (9)	−0.0035 (10)
C8	0.0529 (10)	0.0559 (10)	0.0445 (9)	0.0026 (8)	0.0273 (9)	0.0014 (8)
C9	0.0408 (9)	0.0534 (10)	0.0433 (9)	−0.0030 (7)	0.0242 (8)	−0.0071 (7)
C10	0.0587 (12)	0.0980 (16)	0.0542 (11)	0.0093 (12)	0.0349 (10)	0.0124 (11)
C11	0.0525 (12)	0.0875 (15)	0.0519 (11)	0.0106 (10)	0.0226 (10)	0.0141 (11)
C12	0.0395 (10)	0.0748 (13)	0.0626 (12)	0.0098 (9)	0.0227 (9)	0.0021 (10)
C13	0.0409 (9)	0.0652 (11)	0.0542 (10)	−0.0010 (8)	0.0280 (8)	−0.0045 (9)
C14	0.0375 (9)	0.0542 (10)	0.0400 (8)	−0.0046 (7)	0.0210 (7)	0.0040 (7)
C15	0.0403 (9)	0.0629 (11)	0.0487 (10)	−0.0006 (8)	0.0245 (8)	0.0053 (8)
C16	0.0403 (10)	0.0791 (14)	0.0584 (11)	0.0024 (9)	0.0277 (9)	0.0208 (10)
C17	0.0481 (11)	0.0823 (15)	0.0605 (12)	−0.0146 (10)	0.0237 (10)	0.0190 (11)
C18	0.0746 (14)	0.0596 (12)	0.0589 (12)	−0.0203 (10)	0.0292 (11)	−0.0003 (10)
C19	0.0645 (12)	0.0581 (11)	0.0536 (11)	−0.0049 (9)	0.0344 (10)	0.0005 (9)
C20	0.0799 (17)	0.123 (2)	0.132 (2)	0.0221 (16)	0.0802 (18)	0.047 (2)
N1	0.0420 (8)	0.0610 (9)	0.0584 (9)	−0.0034 (7)	0.0304 (7)	−0.0005 (8)
N2	0.0450 (8)	0.0583 (9)	0.0599 (9)	−0.0028 (7)	0.0314 (8)	0.0045 (7)
N3	0.0379 (7)	0.0515 (8)	0.0450 (7)	−0.0017 (6)	0.0249 (6)	0.0015 (6)
N4	0.0491 (9)	0.0881 (12)	0.0516 (9)	0.0111 (8)	0.0313 (8)	0.0086 (8)

Geometric parameters (Å, º) top

C1—N2	1.317 (2)	C11—C12	1.368 (3)
C1—N3	1.369 (2)	C11—H11	0.9300
C1—C3	1.470 (2)	C12—C13	1.375 (3)
C2—N1	1.310 (2)	C12—H12	0.9300
C2—N3	1.368 (2)	C13—H13	0.9300
C2—C9	1.472 (2)	C14—C19	1.375 (3)
C3—C8	1.383 (3)	C14—C15	1.379 (2)
C3—C4	1.393 (3)	C14—N3	1.444 (2)
C4—C5	1.379 (3)	C15—C16	1.388 (2)
C4—H4	0.9300	C15—H15	0.9300
C5—C6	1.373 (3)	C16—C17	1.381 (3)
C5—H5	0.9300	C16—C20	1.504 (3)
C6—C7	1.375 (3)	C17—C18	1.375 (3)
C6—H6	0.9300	C17—H17	0.9300
C7—C8	1.375 (3)	C18—C19	1.390 (3)
C7—H7	0.9300	C18—H18	0.9300
C8—H8	0.9300	C19—H19	0.9300
C9—N4	1.346 (2)	C20—H20A	0.9600
C9—C13	1.384 (2)	C20—H20B	0.9600
C10—N4	1.335 (3)	C20—H20C	0.9600
C10—C11	1.383 (3)	N1—N2	1.387 (2)
C10—H10	0.9300

N2—C1—N3	110.12 (15)	C13—C12—H12	120.5
N2—C1—C3	123.56 (16)	C12—C13—C9	119.16 (18)
N3—C1—C3	126.29 (15)	C12—C13—H13	120.4
N1—C2—N3	110.15 (15)	C9—C13—H13	120.4
N1—C2—C9	123.91 (15)	C19—C14—C15	121.67 (16)
N3—C2—C9	125.86 (15)	C19—C14—N3	119.22 (16)
C8—C3—C4	118.92 (17)	C15—C14—N3	119.10 (16)
C8—C3—C1	122.00 (17)	C14—C15—C16	120.07 (19)
C4—C3—C1	119.04 (17)	C14—C15—H15	120.0
C5—C4—C3	120.3 (2)	C16—C15—H15	120.0
C5—C4—H4	119.9	C17—C16—C15	117.99 (19)
C3—C4—H4	119.9	C17—C16—C20	121.9 (2)
C6—C5—C4	120.2 (2)	C15—C16—C20	120.1 (2)
C6—C5—H5	119.9	C18—C17—C16	122.09 (18)
C4—C5—H5	119.9	C18—C17—H17	119.0
C5—C6—C7	119.64 (19)	C16—C17—H17	119.0
C5—C6—H6	120.2	C17—C18—C19	119.6 (2)
C7—C6—H6	120.2	C17—C18—H18	120.2
C8—C7—C6	120.8 (2)	C19—C18—H18	120.2
C8—C7—H7	119.6	C14—C19—C18	118.5 (2)
C6—C7—H7	119.6	C14—C19—H19	120.7
C7—C8—C3	120.15 (19)	C18—C19—H19	120.7
C7—C8—H8	119.9	C16—C20—H20A	109.5
C3—C8—H8	119.9	C16—C20—H20B	109.5
N4—C9—C13	122.49 (17)	H20A—C20—H20B	109.5
N4—C9—C2	116.73 (15)	C16—C20—H20C	109.5
C13—C9—C2	120.72 (16)	H20A—C20—H20C	109.5
N4—C10—C11	123.52 (19)	H20B—C20—H20C	109.5
N4—C10—H10	118.2	C2—N1—N2	107.66 (14)
C11—C10—H10	118.2	C1—N2—N1	107.09 (14)
C12—C11—C10	118.65 (19)	C2—N3—C1	104.97 (13)
C12—C11—H11	120.7	C2—N3—C14	127.64 (14)
C10—C11—H11	120.7	C1—N3—C14	127.40 (13)
C11—C12—C13	119.03 (18)	C10—N4—C9	117.14 (16)
C11—C12—H12	120.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···N2ⁱ	0.93	2.60	3.375 (3)	142
C20—H20A···N2ⁱⁱ	0.96	2.62	3.549 (4)	163
C10—H10···Cg1ⁱⁱ	0.93	2.72	3.646 (3)	175

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x+2, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₆N₄
M_r	312.37
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	11.246 (3), 9.377 (2), 18.956 (5)
β (°)	124.655 (16)
V (Å³)	1644.3 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.65 × 0.50 × 0.27

Data collection
Diffractometer	Rigaku SCXmini diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.787, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	16277, 3751, 2691
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.162, 1.06
No. of reflections	3751
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.23

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PRPKAPPA (Ferguson, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···N2ⁱ	0.93	2.60	3.375 (3)	141.5
C20—H20A···N2ⁱⁱ	0.96	2.62	3.549 (4)	162.7
C10—H10···Cg1ⁱⁱ	0.93	2.72	3.646 (3)	174.5

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x+2, y+1/2, −z+3/2.

Acknowledgements

We are grateful to Jingye Pharmochemical Pilot Plant for financial assistance through project 8507041056.

References

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